Music maker, product leader, writer & technologist based in central MA, USA. Tinkering with the internet in pursuit of creative independence.

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2020-03-11 ∞

I made a podcast about product

So I’ve been busy making a podcast.

I’ve also been a little depressed, infuriated, overwhelmed, grateful, loopy. A real who’s who of feelings. Typical for these days, I imagine, but it had gotten in the way of writing.

A significant coping mechanism I’ve embraced during the pandemic is to accept the reality of things, and then avoid thinking about them by doing literally anything else productive with which I can fill time. I started (finally) recording music again. I bought and tinkered with a Raspberry Pi to run more smart home nonsense, a media server, retro games emulator and security camera all in one. My wife and I started a garden. I built a fence around said garden.

I’ve always had a serious itch for the podcasting game, though, due to my love of hearing people I respect ramble on, unfiltered about really interesting stuff, and the sheer exercise of recording audio. Fortunately my friend and former colleague Ben seemed to as well, and we both had some things to talk about.

So we started one called Product Therapy, which is pretty much what it sounds like: two product guys talking out some things that excite us, frustrate us, and others we can’t really make sense of about the kind of work we’re doing. We noticed that while there are a ton of business, tech & even product-themed podcasts out there, there’s virtually none which get into the really messy stuff about it — the reality of doing the job every day. Everyone seems intent on interviewing leaders of the tech giants, sharing killer insights, and the like.

We’ll ramble a lot, and we hope you find it entertaining and perhaps helpful (even if you’re not a product manager). It’s available everywhere you find podcasts:

You can also subscribe directly to our Substack page, which is a cool way to directly show your support, plus a way to get members-only episodes if we ever decide to do that.

announcements product management


2020-03-09 ∞

Clarity is out the disinfected window

I don’t know about you, but I am very overwhelmed at the moment and pretty much all the time. Leave it to a global pandemic to cause people to fundamentally reconsider how people work and communicate and live their lives.

I’m not personally leading a vastly different life compared to how it was two weeks ago: working remote in a farm town with no close friends less than a 45-minute drive away doesn’t really lend itself to lifestyle changes in the face of a highly contagious virus. I’m not even terribly stir-crazy, since our puppy Rosie is getting me outside four to five times a day to urinate, defecate and/or run around the yard.

But I’m feeling a different stir-craziness, one that is much more psychological. My mind is racing constantly despite multiple attempts to calm it down. I am exhausted at the end of every day, passing out in my bed but somehow waking up feeling poorly rested. It took something like seven attempts to even get this short and not-particularly-groundbreaking post together.

I referred back to my clarity” note which drove my goals for 2020, and pretty much everything is out the window at this point: it’s a struggle to be intentional, I’m not reading, I’m not actively creating, breathing only helps for a few minutes before this weird reality sets back in. The only thing that is progressing is my ability to let anxiety about homeownership go, simply because it’s the last thing on my mind right now.

I am having visceral urges to create something but I can’t form a single complete thought around what I could do. It almost feels like the entire world is up for disruption, so there’s a need (or opportunity?) to create things in these trying times, but I can’t achieve the level of mental fortitude required to actually do it. It’s a struggle to come up with an original thought when everyone is seemingly feeling the same: either I am terrified and confused” or I refuse to acknowledge this reality.”

I don’t really have anything to share for insights, advice, or reflection that hasn’t been already shared. If this experience has taught me anything, it’s that the Internet is wonderful for not feeling alone, but it kind of sucks if you’re feeling the urge to do something original.

But mostly I thought the title of this post was cheeky, and wanted to post it for that.

personal


2020-03-01 ∞

Earworms

I don’t want to talk about work or technology or bettering oneself. I want to talk about the thing that was stuck in my head for the majority of the past week, which was the following phrase: We can’t find the books; they must be in La Jolla.”

This is from a sample used in the song If Not Now, Whenever” by The Books, a wonderful experimental folk duo that was moderately popular in hipster circles in the early-mid 2000s. The song itself is fine: pretty repetitive, hypnotic melody, a little boring but also fun for a deep cut. There’s a seemingly random string of voices throughout the song — they don’t tell a story from what I can tell, but the end of one phrase seems to lead into the next. This sample comes up randomly in the middle in the song, after a few old women asking about the books.” It’s unclear whether this is a meta-reference to the band or a commentary on how people consume media.

I don’t know what else it could be, but the phrase just sounds good to me. It sits in the rhythm really nicely, and it’s spoken sardonically and cool. It’s not some deeply catchy, intricately-produced melody manufactured to optimize profits; it’s a passing sample likely meant as a joke.

I have a horrible habit of getting small parts of songs stuck in my head for long periods of time, and then having those songs incessantly distract me.

I just discovered Poppy, whose whole vibe and backstory is insane, and essentially put out a melodic death metal record. There are parts of her new album I Disagree which are certainly catchy, but metal rarely captures my attention these days. I’ve had various parts of the lead track Concrete” stuck in my head for weeks (something about that sugar on my teeth” line), and recently became obsessed with the refrain from Fill The Crown.”

Back-to-back with Poppy has been You Make My Dreams” by Hall & Oates. Talk about a topic jump: from being ironically buried alive in concrete, I move to a simple love confession. I’ve had this track on-and-off stuck in my head since 2016, when it was on seemingly infinite repeat during my best man’s own bachelor party. There’s no need to explain what makes this song an ear worm: it’s probably stuck in your head too from time to time. One scientist calls it a cognitive itch,” which seems appropriate for this particular track.

Cognitive itching seems overall appropriate for the whole sensation inspiring this post. Instead of scratching a technical itch or a career itch, I find myself regularly and incessantly scratching sonic itches in my brain. Sometimes this comes to the detriment of one of those other itches; I think my inability to parse Swift documentation and make sense of inexplicable bugs partly relates to my brain being distracted by those melodies and samples that won’t leave.

Some of these songs are incredibly catchy and have fair right to be called earworms, but others get stuck in my head for seemingly no reason whatsoever. I said the word cocoon” this morning, and now I have Cocoon” by Björk stuck in my head. It’s not even that catchy of a song; her vocal melodies are usually more meandering than crisp. (This was not written for effect — this specifically happened at 8am this morning, Monday, March 2nd.) I’ve been following the pianist/MC Jason Charles Beck (aka Chilly Gonzales) for a while, and I’ve had his track I Am Europe” stuck in my head recently. It’s got a somewhat catchy piano riff, but vocally there’s nothing to hang onto whatsoever: there’s a weird string of spoken-word metaphors in the middle of the song that ring quite hollow (“I’m a dog shit ashtray”; I’m a toilet with no seat, flushing tradition down”), but the piano line, undercut with pitched moans, just works for me. I haven’t listened to this song or album in years, and there’s no reason for me to either –– it’s not that great. But it’s in my head.

Sometimes the nature of these earworms are subtle and specific. Another song I frequently get stuck in my head is You With Air” by Young Magic, which is fun and catchy as hell. It shares a vocal line almost identically with Purity Ring’s Grandloves”, but I rarely if ever think about that song. I have no idea why, despite having the Young Magic version of the line in my head frequently. The context of the backing rhythm and overall vibe seem to matter.

It feels narcissistic to get one of my own songs stuck in my head, but I have a little guitar and bass line loop stuck in my head. I guess one could call that part of the songwriting process, but this particular loop has been in and out of my head since 2009. I guess you could call it catchy once the vocal melody is attached, but the guitar loop is kind of nothing on its own. I can’t explain it, which I guess is the whole thesis of this post. (I guess it’s also weird to link to said song in my own newsletter. Shameless.)

I wonder what some earworms tell me about my inner demons. I have a strong distaste for horror movies –– inexplicable gore and chaos make me very uncomfortable –– but sometimes I’ll scratch an aural itch that would be terrifying to most people. Mr. Bungle, a bizarre, fun and sometimes confusing band from the 90s recently announced a small set of reunion shows in California which prompted me to revisit some of their music. I recently got stuck in my head a song of theirs called Carry Stress In The Jaw”, a song about grinding one’s teeth during sleep, specifically the jittery saxophone line that begins the song and a bit of the following verse. Any rational person would likely find this song terrifying, between the jarring tonal & genre shifts, the chainsaw-sounding guitars, and Mike Patton’s meandering recitation of an Edgar Allan Poe excerpt which builds to a high-pitched wail. But I find it a fascinating and ultimately entertaining listen, and I apparently get fixated on parts of it from time to time. What does this say about me? The aforementioned Poppy tracks are unconventional and dark but ultimately (as her moniker states –– hey!) poppy and interesting social commentary; Carry Stress In The Jaw” is chaotic, strange, and sometimes gross without a clear point. Is this a reflection that my mind is in a proverbial gutter? Is this a manifestation of the actual teeth-grinding I do while I sleep? Am I a glutton for aural punishment?

More likely I just am fascinated by sound, but I can’t help but worry about my sanity with a track like this.

I made a playlist of these songs that I keep pretty up-to-date, for those interested; there’s a lot rattling around in my brain. Check it out here.


This was fun to write. I didn’t really learn anything for have any nuggets of value to share, but it was nice to shove stressful or effortful things aside and just ramble about songs I like. We should be doing more stuff like this.

essays culture


2020-02-24 ∞

Found my stuff

I’m incredibly lucky to have a little bit of time to pursue hobbies or interests outside of my work and family life. One of the interests I’d been exploring was app development: I am deeply in love with the iOS/iPadOS ecosystem and have always wanted to tinker within it and contribute to it. Plus, I’d played a little with development before by running a few Wordpress sites in the past, doing low-complexity coding and bug fixes in previous gigs, and spending most of my workweek talking with other developers for a job. And I had an idea for an app that would actually be useful to me.

So I tried picking up Swift and SwiftUI to develop said app. After about 10 days I’ve given up. I either don’t have the brain, or the patience, for software development. I get the model-view-controller framework completely — I need to at least understand this concept to do my day job, but while I can sort of read code, it’s a whole order of magnitude of complexity for me to write it and not run into a dozen build failures or inexplicable crashed. The place where I got stuck, specifically, was around supporting Siri Intents: the idea involved needing to talk to Siri, or build Shortcuts, around locating a specific piece of data, and I got incredibly frustrated trying to figure this out. Tech pundits are right when they say Apple’s documentation is not useful, and I don’t have the skillset to adapt examples from other people to my own use cases.

The idea stuck, though. It came out of an episode of the wonderful Reconcilable Differences podcast. In this one, John Siracusa talks about his use of Apple Notes to keep a running list of where random things are in his house. Turns out I could have used one of those: My wife and I move random items around the house regularly and then forget where we put them. Some of these are easy to track down, such as AirPods or our phones, because we can yell out to Siri and then a loud bell will be emitted from said device. I wanted to be able to yell out to Siri, Where’s my goddamn box cutters?” when I have a dozen cardboard boxes to break down and can’t find them. The only options I could think of were to buy a Tile or wait for Apple’s competing product, but I also don’t want to spend hundreds (possibly thousands) of dollars putting a Bluetooth tracker on all my tools, random cables, passport, etc. Not to mention all the problems with Bluetooth security and electromagnetic radiation in the house.

So instead of frustrating myself endlessly trying to build a swanky app to solve this problem and then monetizing it for no good reason, I built a group of shortcuts to help me with keeping track of shit around the house.

Found It, the shortcut suite

Collectively they’re called Found It, and they enable you to securely tell Siri where your stuff is around the house. When you can’t find one of those things, just ask Siri and she’ll tell you. If you put that thing somewhere else, just tell Siri and she’ll remember next time you can’t find it.

If you like, you can tap on the links below to download Found It and all its components:

From there, you can start tracking your own stuff. These shortcuts also support custom inputs, so you can make your own mini-Shortcuts that ask Siri for a specific item (so you don’t have to re-specify every single time). For example, I made a shortcut to ask Siri Where’s the hammer?” since I keep leaving my hammer in random places around the house, and she’ll just tell me that. You can get that example here; you’ll just need to tell Siri where your hammer is first.

The master shortcut is available on RoutineHub, which is a community and directory of crazy-powerful Shortcuts.

If this is interesting to you, let’s talk

I’ve realized over the past week that Shortcuts creation is basically a lightweight form of programming, and it’s proven very helpful in the solving of everyday problems around the house. I’m going to be writing more about my explorations here (like some people are already doing — see Federico Viticci or Matthew Cassinelli for just two great examples). If you have a problem you need solving and I might be able to help you solve it with a Shortcut, or if you just find this interesting, let me know or subscribe to this newsletter. Thanks for listening!

announcements tech


2020-02-17 ∞

So, layoffs are weird

This past week my previous employer laid off roughly 3% of its staff. A lot of people lost jobs, and I personally worked with about two dozen of them and knew those folks pretty well.

😞

I’m not going to pretend that this was a massively unexpected surprise; this is absolutely something that happens with over-hiring and mismanagement of performance for large groups of skilled employees. I’m surprised it hadn’t happened already, to be completely honest. But I can’t ignore the fact that layoffs are a really weird thing and I’ve been thinking about it more than I care to in the past few days.

Layoffs are especially weird in 21st-century society, in that we’re able to easily rally for each other on a social network and get out of laid-off status in a matter of hours. I posted twice on LinkedIn offering to help or talk to anyone affected by the layoffs, and these were by far the most popular posts I’ve ever made on a social network, ever. Not only did laid-off folks appreciate it (I spend much of yesterday afternoon responding to folks looking for tips on remote work), but dozens of former colleagues, current colleagues and people I’ve never met liked and commented on what I had to say. Most of those people also had their thing to say, and most of the thoughts were exactly the same: offers to help or talk, the processing of many feelings” with ultimate optimism and gratitude.

It almost feels compulsory, that you must post about one of these things because everyone else in your circle is already doing it: if you’re not grateful to the employer that laid you off, you’re an ass. That compulsory feeling leads it the emotions feeling fake. I genuinely do want to help because I think a lot of highly-skilled and intelligent people aren’t aware of the possibilities out there beyond open office environments at well-intentioned-but-sometimes-overzealous e-commerce companies. I also want to make sure folks are okay with expressing frustration or constructive criticism at their previous employers, because without that it’s hard to imagine companies getting smarter about how they hire and evaluate the need for teams & individuals if everyone’s grateful for the company that took away their lifeline on a moment’s notice.

At least people come together to help each other in the face of a bad situation.

I saw some recruiter posting about a job fair for the folks affected, and his post mentioned layoffs at another company. I then started digging and realized just how many companies — large, highly-reputed, tech companies — are growing too quickly or cannot meet the demand of the market in which they compete. Tripadvisor had layoffs last month, AthenaHealth did last year, so did State Street, and there are rumors flying around that LogMeIn also did recently. Turns out dozens of Boston-based companies have had pretty major layoffs in the past decade.

Another friendly reminder that the primary goal of these businesses is to grow and profit, and the care of its employees is predominantly secondary. If you can find a place where you’re felt taken care of well enough, then good on you.


It’s hard to be helpful in a way that doesn’t feel alienating to someone. Here’s an attempt.

Some advice to anyone who was surprised by it: pay more attention to your employer’s hiring goals, earnings calls, performance review process and the perceived performance of those around you. You’ll quickly realize that there’s plenty of places from which to trim fat in a pinch.

Or here’s some other advice that I’m working on myself: make it so that a layoff doesn’t affect you. This can be done in multiple ways, but here are two I’ve really focused on:

  • Pay very close attention to how your current or next employer runs things: how it spends money, its hiring goals, how it runs performance evaluations, where its profits come from. Ask questions if you don’t understand things or don’t find the information you’re looking for. If you can’t get answers, think about why you’re not getting answers. Ideally, you’ll find a company that is clear with how it runs things and that aligns with your values.
  • Don’t be confined by where you live. Yes, relocation can be hard, but also, remote work is very much a thing that you should not ignore. A quick search with the right keywords (think remote position jobs”) will net you some interesting stuff to consider. If you like being in an office, coworking spaces do exist, and some companies will even cover this expense if you play your cards right.
  • Build up safety nets in other work, and, if you can, find a job that will enable you the time to do this. This is the classic side hustle argument. Most people I know who work in tech are so consumed by their work that it feels impossible to make time to do things on the side. My advice? Unless you truly love your work, don’t work for companies that consume you. My previous employer was one of those, and while I loved the work for a long time, once I stopped loving it I needed to get out.

I’ll stop talking now.

work essays


2020-02-10 ∞

Everyone’s a workaholic

There were multiple nights in January during which I wanted to work on one of those things I resolved to start doing this year, but sometimes one just wants to watch a wonderful television show or spin a record. But there persists a nagging feeling. An itch not being scratched.

I have a lot of itches. One involves forming chords on a piano keyboard, another involves what you’re reading right now, another involves automating my house, another involves just building something cool. I’m not a skilled coder, but I’ve wanted to become good at it so I could eventually make an app on my own. And then I realized that nocode is a thing: No-code development, the idea (or now a movement, I guess) that there are dozens of cheap, scalable services out there on the Internet now which can be strung together to form a meaningfully viable business operation.

I could spin up an idea of my own in a weekend.

I assumed correctly that I’m incredibly late to the party: Personalities on Twitter spinning out consulting services to help fellow no-coders, whole premium communities where indie hackers bounce ideas and team up. But virtually everyone I see on the internet talking about something they love is talking about their paid vocation.

This is not just isolated to weird, specialty forums, but has also taken over my Instagram. I have reached the point where Facebook’s own app — yes, the app that my mother and her friends use more than people my own age — is more useful to me than Instagram, because Instagram for me has devolved into nothing more than puppy pics and individuals & corporations trying to convince me to buy things. Facebook is at least where I can talk to extended family or learn about delays in trash pickups & snow emergencies in town. On Instagram, every fourth story is a sponsored ad, and my feed is roughly 75% people promoting their new albums/projects/products/hustles/whatever. My wife’s feed is even worse.

It’s worse now that it’s extending into the real world. My wife and I need to make a conscious effort not to talk shop while eating meals. The most troubling example: We received a Christmas card from some friends (intentionally keeping theme anonymous), and they were promoting a product in. The. Christmas. Card.

Everyone selling all the time can’t be good for us as humans. Talking only about your work all the time inherently adds massive stakes to virtually every conversation you have; your life is centered on your income, your lifeblood. Sure, eventually some of those side hustles could become sustainable, passive income, and that’s the dream. But think about the psychological damage this is probably giving us.

No wonderful mindfulness apps are so popular: it’s not that they’re fashionable, it’s that all of us are regularly on the verge of a psychotic break.

I truly hope my fellow millenials have hobbies they can pour this anxiety into. The beauty of a hobby is that, if I lose interest, or if my interest changes shape, there are no stakes. I can morph that hobby as I please and as my passion for it changes. When I decided to stop exploring music as a profession, it didn’t stop me from playing; when I decided I no longer enjoy live music, I kept recording music and listening to recorded music. I listen to new and old music constantly; I strive to engage in deep conversations around why great music is great. But I gave up on trying to make money on it, and .

But then again, maybe I should be trying to: I could have done this. There’s the fucking itch again, and here comes the psychotic break.

Instead,

I might start buying Lego sets again and writing about that. Would that get attention?



2020-02-03 ∞

Clarity check-in

And here’s month two. There’s a beautiful partly sunny sky outside but I’m instead staring at an iPad screen. Just kidding, I’m oscillating between the two because the outside is nice.

My theme of the new year was about striving for clarity, and reflecting on the first month of the new decade, forced weekly writing seems to be helping achieve this. I have a bit more clarity around how and why I think about things, what things I want to spend time thinking about, and how I want to convey them.

One thing I’m not thinking about is the Super Bowl, which is a waste of my time.

I have a few larger topics I’m noodling on for future posts, but for now I have some updates on how the year is going so far, and some things I’ve enjoyed along the way.

insert subscribe button

Not doing things is doing things

I did write down some resolutions-of-sorts back on New Year’s Day, in the spirit of that theme. A few are progressing fairly well: writing regularly, being more present for my wife, stopping & breathing more.

Others… well, I have enough clarity to know I don’t care to move those forward at the moment. They’re simply not as important to me as the ones in focus right now. These are things I’m not doing:

  • Participating in a band/musician/songwriting group. I’ll probably write more about this later, but I’ve been rethinking what kind of music I want to make after becoming inspired more by ambient & solo piano music than recent popular music. This is an area for which I am working toward clarity but haven’t gotten there yet. Once I figure this out, I’ll explore this or whether it’s even going to add value to my music composition.
  • Finding something with which to spoil myself. I wrote this down at the behest of my wife who suggested I should do more for myself, and I agreed, but this has been difficult to give priority. I honestly feel like getting a puppy was a splurge.
  • Cultivating an online base/community/whatever. I see this newsletter as something to contribute here, but also I simply don’t care too much to self-promote — I’d rather just write what I feel and see if it sticks.
  • Reading regularly. I started a fiction book and it’s at my bedside, and every time I go to read it I’m asleep in five minutes. Damn you, comfortable mattress.

One area I’m still working through is more strategically defining my relationship with capital-w Work. Working remotely is wonderful and I’ve even grown comfortable with being a bit scattered about it, but I realized early this year that I was so excited about remote work that I neglected to think about what else I might want out of my job. To me, this is not about leaving my job for something better (because no job is perfect but working for Abstract is quite great), but ensuring that I’m being clear, proactive and assertive about what I expect out of the job and how I want to shape it. I’m circling around this idea now, and not sure how it will work out.

Quick aside: Stay tuned” is an obsolete phrase and let’s stop saying it

I was about to end that last paragraph with Stay tuned.” It felt immensely weird to say that, for two reasons:

  1. I loathe the idea of demanding my tiny reader base to be attentive to my bullshit
  2. When I publish my next update, an email will appear in your inbox. You don’t need to stay tuned at all; it will just appear.

Stay tuned” is no longer a thing we need to do because, other than cable TV, our technology no longer warrants it. From Quora:

Back in the day of radio broadcasting, before the era of automatic frequency control (in the radio tuner) a station would drift’ and the listener would have to move the tuner dial ever so slightly to hear the station loud and clear (remember the strength and clarity call out 5 by 5, in which each was evaluated on a 1 to 5 scale, with 5 being the best). Atmospheric propagation would also cause the station to surge and fade at times.
…Now enter the role of the sponsors of the radio program. Each sponsor would be billed a certain amount based on the number of ears” that the program would deliver”. If the number of listeners dropped, the sponsor would pay less and the radio stations income would also drop. It was certainly in the radio stations best interest for listeners to stay tuned to the program - and it would sometimes take a dedicated effort on the part of the listener to stay tuned’.

Internet people: Let’s stop saying this, k? It’s not relevant for our medium. Honestly, it makes us sound desperate for someone’s attention. Might as well say don’t forget about me.”

Ambient Essentials is the best music for not being distracted

The best thing — no surprise — has been shutting off the TV and instead listening to music. Turns out when something isn’t visually distracting you, you’re less distracted.

I truly madly deeply love music, but sometimes it’s also distracting. The one exception that has one-hundred-percent delivered on not distracting is Apple Music’s Ambient Essentials playlist. This is a wonderful mix of highly repetitive, calming pieces that both engross me and allow time to pass without me even noticing. Case & point: William Basinski’s forty-minute-long dlp 6” and Ekkehard Ehlers’ heartbreaking Plays John Cassavetes II.”

Oh, also, sorry — not a Spotify user. There’s a comparable playlist there, though, for all you folks.

BoJack Horseman is over and I’m sad, plus other recent great TV

I’ve started to more deliberately watch TV less and at specific times, which has admittedly been a challenge because there’s so much damn good TV. Just in the past 1-2 weeks, here’s what I’ve enjoyed a lot:

  • BoJack Horseman, season 6 part 2. This has been arguably my favorite show of the 2010s, and I’m sad to see it go.
  • The New Pope. The pace is slow, but the cinematography is beautiful and the premise is incredibly interesting to watch.
  • Servant. I haven’t enjoyed psychological thrillers much lately, but this one has just enough to keep intrigued, between the creepy nanny and the amazing food/cooking shots.
  • Broad City. This isn’t new and I loved this show when it was current, but Alicia and I began rewatching it as the show we could use to laugh out loud when no other show would… including The Good Place which ended strong but not hilarious.

I’ve noticed a recurring theme in these shows as being powerful and immersive, but still escapist. Little America on Apple TV+ seemed good, but it’s too real-world (and somehow feels problematic despite the intent) for me to enjoy right now.

The fewer tools, the better

Like Viticci has been touting recently, and Merlin Mann so eloquently put in a recent episode of Back to Work, I’ve felt a higher degree of clarity by resorting to basics instead of elaborate tools when it comes to my devices & apps. I first tackled this for my online presence, which is no longer beholden to unreliable web hosting providers, and simpler too as a result. I already tweeted about this, so in the spirit of not repeating myself:

The biggest burden w/r/t tools has been how I plan & keep track of what I need to do every day. For a while I used Things to meticulously organize & track those things. It’s a beautiful and quite capable app, but it overwhelmed me constantly. So I pulled everything out of it and moved it all into stock Reminders and Notes. I was already using these to share basic lists with my wife (groceries, shopping, some house project stuff), and when I realized I don’t need to hold myself to arbitrary deadlines for most things in my personal life, I realized the incredibly simple ecosystem I had for myself.

Things that must take place on a day or at a time are in my calendar. I religiously use calendar notifications, even for personal deadlines like posting this newsletter.

Things I need reminders about end up in Reminders (woah). I don’t need a special methodology to organize and categorize those things to do. Notes acts as a reference, a system of record, things I occasionally need to look up: like house utility information, useful shortcuts tips, gift ideas. Sure, I could categorize and tag these things incessantly, but I can also just search for them.

Everything that isn’t obviously a task needing a reminder or a reference note starts in Drafts, which is the one exception to this first-party rule. I like Drafts for a few reasons:

  • Capturing an idea reliably from my Apple Watch is the best thing, and it’s the most reliable way to do this.
  • This thing can format, merge move and prepare text for use literally anywhere, including Substack (on which this newsletter is hosted), which has neither an app or an API.
  • Virtually everything in this app can be organized as I like and done in one click or keyboard shortcut.

Drafts plays the role of my daily agenda, not unlike the pen-and-paper planners folks used to (and still?) use. I wrote a Shortcut that pulls reminders and events taking place today and organizes it all into a Draft — I run this every morning as part of a larger routine that shuts off the alarm system and turns on a few lights downstairs, so it’s ready for me as I’m starting the day. This prepared draft aggregates everything I need to do, everything that’s going on, into a single sheet. With the Taskpaper format, I can easily cross things off the list or add notes to go through later. For reminders that come up throughout the day, I can also check those off when the notification hits, or I can sync a matching thing on my Agenda back over and kill the reminder if I no longer need it.

This is still evolving — in some ways Reminders feels redundant with Drafts for things that are not time-sensitive, so I might move some of my generic lists over to Drafts, which seems like a common use case for this app. That said, simplifying how I go through my day has helped me take better notes while also feeling less overwhelmed or distracted by apps. It’s also been a fun tinkering exercise.

Here’s a link to the Shortcut, in case it’s helpful to you: Prep Daily Agenda


That’s all I’ve got. Bye!

personal essays


2020-01-29 ∞

Thoughts on thoughts on iPads

They say that if you force a regular habit of writing, good things happen. In that sense I should have posted this on Monday; damn you, life and your sudden obstacles.

Last year was the tenth anniversary of the iPad, and a lot of people wrote about it. A lot of it was purely reflective, but some folks evaluated whether the iPad was a success in those ten years. It’s undeniably a success from a sales perspective, but lots of people seem focused on the question of whether it was transformative: to the way we do computing, to the landscape of technology businesses, to the way people live their lives. There are a lot of ways in which a technology can be transformative, but much of the more critical chatter has been on whether it’s been transformative to the way we work.

John Gruber suggests that the iPad has drastically failed to significantly change industries like the Mac did ten years into its existence, largely due to weaknesses in software interaction design, specifically multitasking. This didn’t sit well with me, and it took me a few days sitting with my iPad Pro to figure out why: mainly that comparing the trajectory of iPad in the 2010s to Mac in the 80s/early 90s feels like a fundamentally fraught, apples-to-oranges comparison.

  1. There is no mention of the fact that Apple computers in the 80s and 90s had no obvious device competition in the market at the time and thus the 10-year anniversary is an unfair comparison to give to the iPad. Solutions for designers effectively did not exist like they did once Adobe’s products for the Mac started coming out, and the iPad needed to compete with two other major ecosystems made by Apple itself: the Mac and the iPhone. We’re still seeing how the iPad fits into the larger ecosystem, but it’s already clear that it’s part of a larger picture, one where all types of work can be done on a suite of devices, each perfectly suited to the task at hand, rather than on a computing device at all. If anything, the type of transformation the iPad begat is different than that of the Mac: where the Mac redefined industries, the iPad helped to redefine the consumer technology ecosystem as being universal and multi-device.

  2. We could talk about work & industry changes, but there is little discussion about the changes iPad is bring to how creators make things and how students learn. I believe that iPad’s contribution in these areas are massive, even if not single-handedly, because they (and netbooks) have made full-on computing affordable to more people. There are countless examples showcasing and communities built around the iPad for photography, music production, live music performance, writing. Sure, these may be more incremental in terms of technological changes, but the iPad has put those capabilities in the hands of more people, without professional training or large budgets, and enabling them to do those things anywhere. Sure, Chromebooks are probably used more widely in schools, but without iPads, would there have been the same competitive push for Google to develop an extremely-low-cost netbook for students?

  3. While multi-tasking on iPad does have issues, I disagree that it is fundamentally broken and I consider it a distraction from the main goals the iPad intends to achieve. I personally believe these interactions quite close and the issues I’ve experienced feel more like bugs and solvable with small improvements. I use multi-tasking almost every day on my iPad and, thanks likely to a bit of muscle memory and self-education. Ten years into the Mac, designers were using Macs for work, but it’s 2020 and I know hundreds of people who still struggle with their Macs and PCs but live and die by their iPads because of how much more intuitive it is for them (again, likely due to the learning curve being lessened by iPhones, but that should not diminish the importance of iPads).

  4. Not really directly relevant, but something I think about a lot: since social media took over most discourse about technology, it seems that most people’s opinions on virtually anything is perceived as more extreme (especially in the negative) than it was in the 90s. We could very well be dinging the iPad and feeling nostalgic about the impact of previous technological innvations because everyone’s senses are being numbed all the time by vitriol nowadays.

Laying all this out, I still do feel like the iPad has a long way to go. But this feels empirically exciting to me in a way that Macs won’t ever feel anymore. It seems unfair — almost unsafe — to hold technologies created nearly 30 years apart to the same rubric, as it runs the risk of dismissing technologies that could be changing the lives of many.

These days, I use my iPad for virtually every bit of computing in my life with three exceptions:

I distinctly use it for the following things:

  • Reading
  • Writing and publishing said writing
  • Taking unstructured ideas and fleshing them out
  • Planning my days, nights and weekends
  • Communication that’s more than 1-2 sentences
  • Viewing and editing photos
  • Starting, and sometimes finishing, song productions
  • All my daily work for my job except for software testing (which, by the way, I can technically do on an iPad via a secure VNC connection to my MacBook Pro for work)

Sure, I could be doing all these things on a Mac (or even an iPhone if I wanted to destroy my hands), but I don’t have to. I can do these things anywhere thanks to a cellular connection, hyperportability, perfectly-tailored apps, and a beautifully designed interface whose quirks are no more problematic than those of any other computing device. And to me, that’s transformative.

See y’all next week!

essays tech


2020-01-20 ∞

A bunch of crap duct-taped together

On the partially smart home, and other dependencies in my life

It’s Martin Luther King Jr. Day, and I have four unused Philips Hue bulbs and I don’t know what to do with them. I bought them for a previous apartment, in which I really wanted to play with Apple’s HomeKit protocol as a means to automatically dim the lights when it’s bed time.

My new house warranted different lights to achieve the same result, and these became redundant. I wanted to use these — the basic white bulbs — for the ceiling fan in our living room. However, the previous owners of the house put in a combination fan/light dimmer switch, and when the dimmer and smart bulbs interact with each other, the bulbs flicker annoyingly. I could replace that switch, but to do so the right way and keep smart bulbs in play, I’d need to convert the one combo switch into two separate switches (one for light, one for fan) because there is no HomeKit-compatible combo switch on the market (or any smart switches of this nature that I’ve been able to find).

There’s no sense using them in the basement. There are already lights down there, and I go down once a week to make sure there are no leaks or ghosts or anything, and then I come right back up.

It’s not worth trying to use them in the garage, where the ceiling nearly twenty feet high and I don’t own a ladder with which I can reach it.

I can’t use them in the office (or rather, the spare bedroom with a desk in it). I don’t have the desk space for a table lamp, and if I put them in the ceiling then they’ll be on the main light switch and I don’t want to deal with HomeKit errors when I accidentally shut the switch off. If I do use them in the ceiling fixture, then I’d need to either have them run on a motion sensor that detects when I’m in the room and train myself to stop using the switch, or replace the switch with a smart one which is more money blown on this stupid pointless really fun experiment.

Should I just buy some floor lamps as an excuse to use the bulbs? This option seems very dumb.

All of these options create more work and don’t solve any additional problems without said work. I could argue that this is a fun, mildly inexpensive hobby, but it’d be an incredibly first-world hobby. It would also be one my wife loathes because of how often I’m tinkering with it, and inadvertently breaking things like our security system or the bedside table lamps.

As mentioned in previous writings of mine, I’ve tried various means to get the things in my life working for me. Instead, they create more dependencies and problems to solve. The house we bought came with Wifi-enabled garage doors, and I bought a SimpliSafe to secure the house. Neither system is HomeKit-compatible, so I jerry-rigged them into the Home app thanks to Homebridge, which required me to first invest in and learn how to run a Raspberry Pi because I didn’t want to have a server running 24/7 on my Mac, and then once I got the Raspberry Pi set up, I needed to figure out how to set up Homebridge, get an externally-accessible IP address, figure out how to do SSH so I can run the robot vacuum since I can’t get that reliably running through Homebridge, maybe set up an optional Plex server now that the Raspberry Pi is actually working, make sure I don’t break Homebridge in the process of setting up Plex, test, test again, test some more, sit down and play with my garage doors.

I think I’ve opened the garage doors twice with my iPhone since setting this up, but when I do, it works great. I do occasionally check the SimpliSafe sensors and set it at night, but a frustrating rate-limit issue on their API causes this to break occasionally and requires me to reset the Homebridge server — which I then built a Shortcut to do in two taps rather than needing to SSH into the aforementioned Raspberry Pi.

(Takes a breath)

I want to believe that this crazy set of dependencies into which I’m throwing myself is unique to the new and exciting Internet of Things. But most of my early adventures in homeownership are proving to require a similar network of dependencies, sometimes optional, mostly required because of reasons I’m not always able to challenge.

Alicia and I wanted to redo the floors in the new house because we had some money left over from our house budget. This was a glorious proposition: we came in way under budget on the purchase and could start turning our moderately-sized house in the sticks into a dream home that would make Pinterest proud. In reality, it’s three months later and the floors are still not completely done, we can’t get them finished until the contractor we hired gets stair parts stained to match the actual flooring, for which he had to sub-contract a different company who effectively gave up on the job, thus requiring us to have to find a second sub-contractor to finish the child task for the parent flooring project which is actually the second phase of an even larger flooring project. All of this because we did not know that flooring manufacturers apparently don’t make stair parts that match their own flooring, despite it likely being a very common use case to install matching stairs and floors. (That seems like bad business. Is that bad business? I don’t even know.)

The adorable little puppy we just got? Even she came with a bunch of things to remember. This isn’t a surprise: dogs are living things. But it’s also basically an entirely new set of commitments and optional-but-strongly-recommended-by-the-rescue-shelter-and-vet activities that somehow also depend on each other. First, these pills, then wait six days then start giving her three pills. Then, another test and maybe she’ll be ready to start training and play school but only if this is all done before she is five months old; if it takes longer, we have to do a different set of things. Day two of owning a dog felt like I just absorbed an entire team at work, and that team was sort of floundering but didn’t really realize they were floundering because they didn’t know any better.

It’s weird: being a guy who helps build products, I thrive on figuring out & squashing dependencies. And I’ve gotten pretty great at doing so in the last few years of my career. It’s incredibly overwhelming, with that in mind, to have introduced so many dependencies into my life all at once with little idea how to tackle them. These things start to feel like a bunch of crap duct-taped together, despite a ton of prep (and money — let’s be honest) to avoid that feeling.

So I’ve started to treat my dependencies like enemies, such that I keep them real close. I actively look for them, I embrace them when I find them. I question why something seems to come together so easily. Sometimes this creates a small anxiety, but I’ve trained my brain to mostly treat these as learning experiences.

Here’s an example: I replaced a dumb light switch with a HomeKit-compatible dimmer switch for the first time last week. The next morning, we had a weird series of brownouts in the house. I immediately thought I caused it with my hackery, until twenty minutes later when I decided to check the electric company’s website which confirmed a regional outage. Power returned fifteen minutes after that. Sigh of relief: it wasn’t my fault, and now I know that my electricity provider can sometimes screw up the voltage in my house.

Time to figure out what the hell it’s going to take to put in a backup power generator.

Of course, some of these things are worth the trouble.


Of course I’m rambling about smart home stuff on an actually important holiday like Martin Luther King Jr. Day. If you read through this whole thing, do yourself a favor and do something nice in the name of universal civil rights, like a donation to the ACLU. Or subscribe to this, because it’s another newsletter to entertain you!

See you next time!

tinkering essays


2020-01-19 ∞

Secret weird things I do

One of my favorite podcasts is Reconcilable Differences, which is a biweekly conversation between two parents in tech/podcasting about their lives. It’s a huge inspiration for this blog.

There is a recurring segment the two hosts (John Siracusa and Merlin Mann) talk about called Secret Weird Things People Do,” in which they talk about just that — not just confessing to the things they do, but also dig into where the weird thing came from, why they do those things, whether it’s actually weird or pretty normal, and the like. I find these discussions incredibly interesting and compelling and humbling.

In that spirit, here is a list of some secret weird things I do:

  • I cannot let my kitchen get messy, and if I do, it viscerally bugs me to the point of a near-anxiety attack. This is especially problematic since my wife is an Italian who loves cooking and has a horrible habit of leaving a huge mess in her wake. Typically at meal time, I am cleaning up as she is making messes — much to her frustration, since sometimes I inadvertently wash dishes she is still using.
  • If I need a reminder to do something (say, in an app), I can’t just add it to a list. I need to pick a time and appropriate category/list for that thing, even if it’s neither easily categorizable nor time-sensitive. Sometimes this bites me when I get a reminder at a horribly inopportune time, but it’s the only way I know how to keep track of things.
  • If you ask me to do something, I can’t listen to the next thing you have to say until I write that ask down. Due to the previous weird thing, this might take me an extra second and I’m sorry.
  • I compulsively look for things to automate, organize or optimize in my home, even if it’s a negative return on investment. (Merlin talked about this in a recent episode.) I spent an absurd amount of time trying to correctly place speakers around our house for audio playback. I rearrange my iOS device home screens almost daily — not for fun, but because I think I’m missing something by how they’re arranged. I track my dog’s bowel movements in a Numbers spreadsheet. I’ve set up part of my home to be smart and I’m not sure it was worth it, but it keeps feeling like something I must do. Sometimes this extends into my wife’s stuff, and she usually gets frustrated with me. I’ll probably write more about each of these weird things later.
  • I compulsively use GPS in my car even when I three-hundred-percent know where I am going and there is no possibility of traffic.
  • I don’t bite my nails, but I pick at them compulsively. Alicia loathes it and slaps/pinches me to get me to stop. I think this used to be a nervous tick, but now it just happens constantly.
  • If there is a stack of books (or book-shaped things like laptops/iPads), I must have them perfectly aligned in the stack. If there is a book in the pile that is slightly rotated, I must rotate it so all the edges are aligned.
  • Despite a lot of my cleanliness-related weird things, I don’t seem to be bothered by objects covered in dust.
essays personal


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