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:

• Using and testing the product I manage for my job;
  
• Taking music ideas to finished product in Logic Pro X, which might become unnecessary over time; and
  
• Running a Homebridge server

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!

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!

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.

Running a dumb robot vacuum with Shortcuts

I love the idea of a totally self-sufficient robotic vacuum to keep my floors clean. However, I am also cheap: [a $1000 Roomba that empties its own waste] is amazing, but not something I’m willing to chalk up for at this point in my life.

So, I got an [Ecovacs Deebot N79] for sale on Amazon a few months ago. It’s great, but it’s also pretty dumb. Alicia and I call it DJ Roomba ([obviously]), and it’s very cute but kind of dumb.

It can schedule itself to run daily at a certain time, but no more granularly than that — I don’t want to hear a vacuum at 11am when I’m at home, but I do appreciate coming home to a clean house when I’m out and about. It does have Wifi capability and a companion iPhone app, but the app sucks: it requires 2 taps and several seconds of delay just to find DJ Roomba, and then I have to tell it what to do, and every time I want it to do something different I need to repeat this entire process.

It’s not great. I’d rather just build a scheme that DJ Roomba can follow automatically, whenever I want it to.

Homebridge and its flaws

I naturally Google’d the crap out of this problem. I quickly found [sucks], a Python interface that connects to Ecovacs’ server and then enables one to issue commands to any robovacuums tied to your Ecovacs account. This was easy enough to set up. I then found a way to [connect sucks to Homebridge via a plugin called CmdSwitch2].

I had never used [Homebridge] before, but I love the potential of HomeKit. I already have a moderately robust HomeKit setup in my apartment: some smart bulbs, a couple of switches (including a critically placed one controlling my modem) and a HomePod to yell at, so installing Homebridge on my Mac seemed like a fun little project.

Turns out I suck at and don’t enjoy the command line. The process of setting up Homebridge, connecting all the dots between Python, sucks, cmdswitch2 as a trigger that exists inside Homebridge’s config, and Homebridge itself, was a tedious process that quickly lost my interest. I kept having to kill and restart Homebridge to make sure everything was playing nice. I must have scanned the Homebridge QR code into my iPhone’s Home app twenty times to get it registered as an accessory.

The other major challenge: I didn’t want my wife to have to deal with this either, but we share an iMac. She uses it regularly for work, and often has to kill processes in order for Adobe apps to run optimally, or restart the computer if things go wrong — which also killed my Homebridge server. I found some options to automatically restart the server, and I could have kept trying those things, but my fun little hobby project of automating control of my dumb vacuum was increasingly frustrating me. I’d go to start the vacuum and constantly see the damn “No Response” in red.

So I gave up and dismantled the entire thing.

A few weeks later I realized that I don’t actually need Homebridge or cmdswitch2 at all. I really just wanted to run sucks on command: ideally a specific times of day or when I’m home, but just being able to trigger it from any of my devices (or my voice) would suffice.

Enter crazy and powerful Shortcuts.

Shortcuts and a simple AppleScript

Nobody I know personally really uses Shortcuts, but it’s sort of my lifeblood for controlling things around my home and work. I use it to set reminders without thinking, do a whole host of chores every morning & weekend, and generate canned email templates that I shouldn’t have to send as often as I do.

[Viticci] opened my eyes to the idea of [Shortcuts triggering actions on a remote Mac via SSH], including waking it from sleep. I figured out that I could also run AppleScripts using the an SSH command — osascript.

I realize that most tech people probably know this already, but bear with me.

I then did the following:

1. On my shared iMac, opened up Script Editor and created an AppleScript (.scpt) file that run a basic sucks command: sucks edge 15 clean 30 charge. This script, when run, tells Ecovacs to run the “edge” function on my vacuum for 15 minutes, then general cleaning for a half hour, then send the vacuum back to its charger.
   
2. Saved that .scpt file my parent user directory on the iMac.
   
3. In Shortcuts, wrote a very simple (1-step) Shortcut that triggers script via SSH. Rather than SSH-ing into the iMac locally, I enable SSH access and file sharing on the iMac, then connect to its IP address so I can run the command from anywhere.
   
4. Repeated steps 1, but with a different script that simply tells DJ Roomba to go home, it’s drunk: sucks charge

Now I have two Shortcuts: Run Vacuum and Stop Vacuum. I can yell out to my HomePod, tap a button on my iPhone or iPad, to kick either process off. As long as my iMac is on, this will always work.

I can run this as part of another shortcut, such as my Bedtime Ritual one which darkens some lights around the home and reminds me to floss, clean out Roomba’s dustpan and a few other things. I can even have Reminders remind me to run the Run Vacuum shortcut at specific times or locations — for example, anytime I leave my house. Then, in one tap, DJ Roomba is up to his antics.

The possibility in iOS 13

This works really nicely, but it’s not perfect. I’d love to customize even further when and how DJ Roomba can run. It sounds like this all gets unlocked in iOS 13 via Shortcuts Automations. I’ll be able to, for example, run the vacuum on Saturdays as long as nobody is home, something I can do currently but only with HomeKit accessories.

This is really dumb and nerdy, but I find it satisfying and fun.

Impostor snowflake

It’s been a while since I finished writing and publishing something. I would love for this to be because I have an exciting thing to announce that I’ve been painstakingly working on for the last however many months.

But I don’t (at this point at least). I have personally nothing to add to the cesspool. (My wife does, though, and you should go to her new website, yay!)

It’s not like I’ve felt no emotions or accomplished nothing in the past year. I’ve gone through a lot — my family has gone through a lot. I moved twice, settled twice, changed roles at my job, put out an album of music. I’ve felt anxiety, rage, excitement and joy through all of it. But none of it seems worth sharing.

Why is that?

I’ve also noticed my unwillingness to share things on social media platforms. I even had to set up a daily habit reminder (in an app called Streaks) to remind me to post a photo at least a few times a week.

Am I depressed? Maybe I’m depressed. Maybe I’m the old soul my wife keeps telling me I am. Mostly it never feels genuine. Except it is — I have real joy that I feel, but usually it’s in small quirks that my wife and I share. The occasional lyrical idea that comes to mind and gets written down but never gets seen by anyone but myself and Apple’s servers. The most public things I do currently are this obscure blog and my day job work, which is conventionally sexy but often feels like something everyone in e-commerce is already doing.

I don’t get off on winning. I get off on originality. Why is it so hard to find that? Am I just too risk-averse to go look for it?

Do people who actually share also exhibit these same feelings? What is the hurdle one must jump over to get past this feeling?

Do I just feel a need to individualize myself? I hate the idea of thinking that I’m a snowflake, but I think I feel awful and not worthy of anyone’s attention because I’m not a snowflake.

Is this ridiculous? Do people feel this?

Gear / Hyperportability

Moving out of the US has forced me to evaluate the gear I use to optimize for portability - but I am still an unabashed fan of the gear I own. Here is the gear I’m currently using to make things.

Hardware

Most of the time I’m doing things on an iPad Pro 10.5” (256GB) or an iPhone 7 Plus in Slate Black (also 256GB).

Heavy music production, code tinkering and design gets done on a late 2013 MacBook Pro with retina display, which I share with my wife. I also wear an Apple Watch Series 3 (GPS only, suckers).

I listen to audio with Apple AirPods or a pair of Sony MDR-7506s. I sometimes still play piano, and when I do it’s on a Korg nanoKEY 61 MIDI controller; on the go, I might bring along a Novation Launchkey 25.

Vocals used to be recorded in a padded closet with a Shure SM-58 fed into an Apogee Duet v3. But now, since my best-available recording space is a closet on the opposite side of my apartment from any reasonable workspace, I opt for a Samson Meteor USB mic, fed directly into my iPad Pro for tracking in GarageBand.

Software

Virtually everything that involves text starts in [Drafts 5], and then usually ends up in either [Things 3], [MindNode 5], Apple Notes, [Google Docs] or a text file edited in [Pretext]. I publish to the web using Wordpress, and sometimes tinker with my websites using Transmit (RIP), Coda or Kodex.

Most of my music is recorded using Logic Pro X or (when mobile, [GarageBand for iOS]). It’s all then backed up via Splice. Occasionally I’ll pull some samples or soft synths from Reason 9. My favorite piano sound is the SONiVOX Eighty Eight, and my vocals sound much better thanks to iZotope Nectar 2 and Stereo Imager.

When on the go or too lazy to sit at a desk, I compose or tinker with song ideas using [iGrand Piano for iPad], the Moog [Model 15], the fantastic drum machine DM-1 or [Novation Launchpad].

32 places to put stuff

I have a lot of places in which I put things I care about.

I use Reminders to store…well, reminders of things I need to do. Basic lists.
I have a wish list of stuff I want to buy on Amazon, but then I have another list of other non-Amazon stuff to buy in Reminders.
I also have a few lists and notes for things in Apple Notes.
I keep my passwords securely in 1Password.
I use Trello to manage projects, but not all projects because not everyone uses that.
For some things, I need to make a Google Doc or Sheet. (Somehow, I’ve literally never had a need for a Google Slides presentation.)
Sometimes those projects have other materials. If I’m collaborating, they get shoved into Google Drive or (occasionally) Dropbox.
If it’s a personal project, it’s most likely iCloud Drive.
If it’s something in Adobe’s ecosystem, it might end up in Adobe Creative Cloud - I barely ever use it, but sometimes things occasionally end up in there.
I use Scanbot to scan papers, receipts and stuff for storage in one of these places
If it’s a work thing, it goes to Sharepoint which also includes a hook into OneDrive.
Sometimes it’s a manual or guide book for something, in which case it goes to iBooks, which is basically iCloud but also sort of not. Speaking of iCloud services and reading, Safari Reading List also houses some reading materials that I care about.

Photos can of course be stored in many places - it doesn’t really matter where they go as long as they’re everywhere all the time. In case they aren’t, well, they start in iCloud Photo Library, then go to Google Photos and Amazon Prime Photos.

All this stuff backs up to one of two external hard drives, and an Amazon S3 bucket.

Sometimes I write. I like Markdown for my own personal writing, so I write lyrics, creative ideas and blog posts like this one in Ulysses.
I can’t use that for my day job, though, so for that I use OneNote to write & share notes & documentation with my team.
We use a proprietary solution for managing technical projects.
Roadmap documents? Excel and Word. Not Trello, at least yet, because I need to get people to adopt it and we’re a pretty tight Microsoft shop. Speaking of which, Powerpoint.
We still use Slack to communicate, and I use it for some other things. Sometimes I save notes and to-dos as starred Slack messages.
Of course, there’s always stuff in one of 3 Gmail inboxes, my work email via Microsoft Exchange.

This is a list of apps in which I can put things I care about. They all have incredibly discrete functions in which they’re invaluable to me, but they all each have storage capabilities too. There’s also all the physical papers and forms and stuff filed away in a bookcase.

Thank goodness cross-platform search technologies these days aren’t awful, because if I had to remember in which place I stored something, I would be lost pretty much constantly. As much as the app economy and tech startups fascinate me, it’s almost too easy to lose track of everything. If productivity tools like Workflow and IFTTT make it so much easier to keep things in sync, and there’s backup solutions galore, why does the digital side of my world still feel so fragmented?

As much as Apple’s plan to store users’ entire Desktops and Documents folders within iCloud for syncing purposes is slightly nerve-wracking, I appreciate the effort to help consumers keep their shit in one place. I realize this anxiety is partly my own neuroses and my being raised on a file system paradigm, but I also have to imagine that the fragmentation of the cloud storage (and general digital storage) markets are part of why tech is so overwhelming for some.

The wonderful future, or my phone is slowly becoming my wallet

Since Alicia and I moved back into Boston proper, I’ve started to hold cash on me much less frequently. Back in NYC or up in Salem, most of the establishments we frequent only accepted certain credit cards; many were cash-only.

Now, I can use Apple Pay or order online from pretty much anywhere I frequent - cabs & Uber, groceries from Trader Joe’s, Starbucks and most other local chains - for everything else, I’m only really using one of two debit/credit cards. My only actual use for cash, except when I’m not in Boston, is to pay my barber every month. This has been a wonderful way to live, if anything because I have to worry about having less with me at any given time. My only further request is that I could get my driver’s license and MBTA subway pass somehow onto my iPhone - then I could ditch my wallet almost completely.

Having a thinner wallet is kind of amazing, but my iPhone is starting to feel like a single point of failure. What if I drop it and crack the screen or damage the NFC chip or the Touch ID button? The 6s Plus has amazing battery life[^1], but what if it dies? Do I replace my wallet with my little Anker portable charger in my back pocket? What if I lose or forget that? What if I get mugged? Or worst yet, what if I lose the phone due to my own idiocy? How will I get my goddamn Venti iced coffee? 

It gets me thinking about product redundancy - the physical wallet begins to act as backup for my virtual Wallet. But what happens when I have no need for a physical wallet anymore, other than to cover my ass if my phone dies? That’s kind of an annoying prospect? Is that what Apple’s betting on with the Apple Watch, if you ignore the lifestyle play? When does the “all-powerful device” with several obvious Achilles heels require redundancy, especially when you don’t want to also carry your phone in an Otterbox case and with a portable charger constantly?

It’s all really fascinating, is all. It’s interesting to me that we still don’t have a good, trusted, redundant solution here that’s also convenient and cheap. We have it with our digital files thanks to name-your-cloud-storage-and/or-backup solution, but credit cards, identification and other highly physical-world things are still confined in your pocket or purse one way or another.

I get excited for our inevitable Minority Report-like future in which we could have public kiosks where, via a retina or thumbprint scan, you could retrieve a temporary copy of your ID, driver’s license, last credit card used, or whatever you lost while out in the world. Dropped your phone and it’s useless? Scan your finger at a Touch ID kiosk and you can automatically have a temporary ATM card printed instantly for use. Got mugged or lost your phone in an unfamiliar place? A quick scan could get you quick access to emergency response care, your Medical ID and history, and/or automatically wipe your phone and notify a loved one that you’re okay. I don’t know nearly enough about the technical complexity of making this work in practice - the scanners would need to be sanitary, damage-resistant, weather-proof, whatever else - clearly there are a lot of holes to this. It’s almost certainly easily hackable if we’re not careful.

But it’d at least be super cool, right?

On Prince’s “The Ballad of Dorothy Parker”

Prince died a week ago. I’m really bummed about it. I’ve had some really good friends rave about how life-changing his shows are, and I kept convincing myself that I’d actually go to one. That can’t happen anymore, and it reminds me to take advantage of what exists in the now as much as I can.

What I have now is his entire discography, pulled together from various sources since I started listening to Prince regularly in my adult life. This past week I’ve been listening almost exclusively to all the Prince music I’ve collected, while also occasionally reading the reflective writing that has been published about the Artist. Much of that writing has been focused around his early-era, groundbreaking synth pop work: Purple Rain, working with The Revolution, the song “1999”. An occasional word about his tenuous relationship Warner Bros. Records. This great piece about the underrated & sometimes bizarre 1981 release Controversy.

I want to talk about one Prince song in particular that fundamentally changed how I think about recorded music: “The Ballad of Dorothy Parker.”

I didn’t like Purple Rain the first time I heard it in full. That was back in 2009 or so. It was so 80s. So many synth sounds. It didn’t really hit me that “When Doves Cry” had no bassline, and what that meant for music at the time, until I read about it in some retrospective a year or two later.

The album that sucked me into the Artist’s oeuvre was instead Sign O’ The Times, which a close friend of mine recommended in 2010 or so. It’s also considered one of his classics, but it’s a weird one: it’s a double album, and while all of Prince’s albums meld all sorts of genres together, this one frequently put wildly contrasting material against itself, back-to-back, almost forcing the listener to fundamentally change listening habits every few minutes. Take “Slow Love” and “Hot Thing,” both on disc 1 - the former is a great albeit typical sexy Prince slow jam, the latter almost a new standard for extreme pop minimalism. The entire first two minutes of “Hot Thing” pretty much centers around F# and a drum machine and don’t change until a bizarre (for Prince) sax solo and frenetic scat-like vocals dominate the mix.

“The Ballad of Dorothy Parker” sits at the end of the first side of disc 1 of Sign O’ The Times, as sort of an ominous closer to a side full of likely hits. The title track was an actual hit; “Play In The Sunshine” is one of the most uplifting and energetic songs released in the 80s; “Housequake” is, despite its strange pitch-shifted lead vocal, an undeniably funky party jam. “Dorothy Parker” almost serves as the hangover after the housequake - it’s barely a ballad, with its frenetic beats and brisk tempo, but it paints a hazy, bleak picture of Prince’s after-party vulnerability.

Susan Rogers, Prince’s sound engineer during this period, recalled in a wonderfully detailed interview that a new recording console at Paisley Park (Prince’s recording studio complex) was not wired up properly when he impulsively decided to begin recording “Dorothy Parker”, and noticed that everything he recorded was coming out dull - no high end, no typical sheen. Prince noticed instantly, but decided he loved it given the fact that he conceived the whole song in a dream, and the dull sound complemented that dream-like quality of the lyrics he wrote.

How does the dream begin? Fuzzy and abruptly, as many do. “Dorothy Parker,” the recording, kicks off instantly with a sped-up drum fill, then silence, then an ambiguous 7th chord that takes a few seconds to resolve to E minor. In fact, every section of the song begins in suspension - when it’s not pivoting to a different tonal space entirely, Prince relies on A7s and F9s to leave you needing resolution, which comes eventually and is often paired with that abrupt drum fill again.

What I love about the “Dorothy Parker” recording is how dirty it sounds throughout. Not dirty in the typically-sexy way that Prince usually injects into all his work - but tarnished, ugly, weak, in repair. The 3 drum machine rhythms that drive the song forward constantly interrupt each other; the bass is hard to identify as synthesized or performed; the chords performed through a weak-sounding tremolo. Every element of the music sounds like it’s falling apart, pushing up against each other, beating itself up left and right, and Prince is trying to corral all the pieces together via his story to tell.

The story, by the way, is also brilliantly ugly in its detail: Dorothy was a waitress on the promenade, working the night shift for a lotta tips. She hooks up with Prince in the form of a shared bath after ordering a fruit cocktail (who does that?) because he ain’t too hungry. There are numerous references to clothes being wet (which is uncomfortable for anyone), keeping his pants on (almost a first for Prince), a violent room. In the climax Dorothy comforts the Artist with Joni Mitchell so he can return to said room. It’s a song about vulnerability in every respect: being uncomfortable, revealing yourself, letting someone in. That’s all a stumbling mess most of the time in reality - not unlike this song’s rhythm section - it takes a lot to say “cool” to a new face, and it’s weirdly specific to ask to keep your pants on in a presumably sexual encounter. Perhaps this was Prince telling us that he wasn’t this perfect sexual being he portrayed in the rest of his material. Who knows.

Prince apparently didn’t know at the time he wrote “The Ballad of Dorothy Parker” that she was also a writer; to me, that discrepancy only adds to the confusing dream the song puts forth. Are these the same women? Is Dorothy a waitress who moonlights as a writer? Does she become a writer after being inspired by the Artist’s violent room experience? Who is this girl, really? In the way that Breaking Bad fans clamored to learn more about the ugly, tragic story of Walter White, I get wrapped up in the story of Prince and Dorothy every time I play this track. If this song taught me anything, it’s that a song does not need to sound polished in order to be great.

The production value (or lack thereof?) gives the song its identity, no doubt. Of course, it’s not as easy to replicate that sound in a live setting - while I hadn’t seen Prince perform live during his life, I’ve seen only one video of him performing “Dorothy Parker” with his band. I think it was on the Arsenio Hall show.

In the live setting, the song transforms into a Latin-infused mid-tempo R&B jam; a salsa-esque saxophone hook brings a sense of direction more than anything in the recording. As great as this live performance is, the emotional center of the song is fundamentally different than its recorded counterpart. Dorothy is still a waitress, but Prince talks to her with a more confident strut.

Perhaps my own social anxiety is why I identify with the recorded “Dorothy Parker” so much; I would never approach someone with that confidence in public. The bleakness of the recording resembles the murky reality of meeting new people: everyone has their baggage, and it’s really uncomfortable and sometimes requires a vulnerability you’re not used to bearing. That vulnerability is lost in most popular music. Some artists might explore it in their lyrics, but there are few examples where the music and its production take the listener to a place beyond the words themselves. Few examples in pop are this ugly.

Let’s hope for more songs like “Dorothy Parker.”

Eight months, in an office

10 months ago, I was living what I thought was a dream: working remotely for a decently-buzzed tech startup where I was the lead product guy. I could work in my underwear, start and end whenever I wanted, have free reign to work and travel wherever I pleased.

Then in May, said startup laid me (and pretty much everyone else) off with a week’s notice.

I had seen this coming for almost a year for various reasons I won’t get into - but what did surprise me was the ease of getting back on my financial feet. Those of us who got laid off were offered a new job pretty quickly by Wayfair, an e-commerce giant also based in Boston. So that’s where I ended up.

Eight months later, I find myself finally in my element again. The first three months in this job were total culture shock: I was uncomfortable around so many people, all of them wanting to talk to me all about the work and nothing but the work. I was frustrated with having to commute to an office at all, let alone walking down the street like I would regularly do in New York.

But over the last few months, I figured out a rhythm to make it work for me. It’s certainly not a perfect situation - but then again, what job is, really? - but I’ve had some time to reflect about being in an office again.

(Disclaimer: this is primarily about the experience of working in an office environment, particularly after a stint in startup culture, and is in no way intended to be a reflection of the work I do, or my employer, at all.)

Wayfair employs thousands of people and has an office right next to Copley Square in Boston. When you walk into the office for the first time, it’s hard to not feel like you’re part of something massive, given just how many people are flocking to the Copley Plaza complex between 8 and 9am. You’d think one of the stores in the Copley Plaza Mall was having a blowout - nope, these are just Wayfair employees trudging into work.

After a few weeks, though, the awe of big company size and impact turns into drone-like fatigue…especially as wintertime sets in. Droves of sleepy, freezing employees passing through subway turnstiles, huddling underneath half-broken umbrellas and avoiding puddles of slush (and being forced above ground to avoid MBTA construction), just to stare at a PC screen and talk in corporate-speak.

Simply having to be at the mercy of weather sucks. When I was working from home, if it was snowing out, I could just stay inside. I technically have the facilities to work from home in my current job, too - so it can be frustrating to eschew all this technological capability just to be present in the office culture. Wayfair has offices in several locations around the US and Europe; I can’t tell you how many times I questioned my battling of snowstorms to get into the office, only to sit on calls with my Berlin colleagues all day.

That said, if you’re stuck on calls all day at home, you might never leave the house. Get this: working in an office forces you out into the world. This is something I completely took for granted as a remote worker - I would occasionally run out to a coffee shop for a while to get stuff done, but nothing was more comforting than parking it on my couch for 9 hours straight save bathroom and lunch breaks.

Speaking of which, when you begin to compare home-work and office-work life, tiny subtle details start to surface about your lifestyle. For instance, The cost of your utilities start to become something you scrutinize monthly - I drastically underestimated how much I was spending to run electricity and heat during the ’14-’15 winter while working at home. Finding food to eat in an office is a really hit-or-miss thing, depending on where your office (or home) is located. I have the benefit of being right near Copley Square, where food trucks and solid restaurants abound. My last office job was in an awkward part of East Cambridge, MA, where our best culinary options were in a mall food court. At home, you’re really at the mercy of your grocery list or what (if any) restaurants are nearby; back in NYC, this wasn’t a problem, but in quieter parts of the world, this could certainly be a drawback.

Everyone who Product Manages knows the difficulty of trying to herd cats - oops, I mean colleagues - toward a shared product vision, and this difficulty is only amplified when doing it from afar. Being in the office ensures presence from everyone who matters, including my/yourself. I find myself more productive overall, simply because I had face time with colleagues working on projects with me - and no at-home distractions, like my guitars or my television. I can also use my commute to unwind and/or focus on things I’d never be able to focus on given those distractions. I’ve started writing again simply because I have over an hour of “free time” on the train every day.

Working in an office can be painfully social. To avoid talking only about the work, you need to find common interests with your colleagues: in Boston, it’s generally assumed that this is Boston sports. If you’re not actively following the Bruins/Pats/Sox (or worse yet, following another city’s team) you’re already at a disadvantage. I’ve come to develop a personal brand around music snobbery, pop culture savvy and a more casual tone, which people seem to appreciate outside of my general apathy for sports.

Once you figure your general vibe out, though, working in an office can be delightfully social. You actually start to make friends and engage in social conversations and outings you never would’ve had sitting at home or in a coffee shop all day long. Sure, there’s spontaneity involved with serendipitously meeting new people at your local coffee shop, but there’s something equally spontaneous in the side conversations that happen at work. My aforementioned music snobbery may manifest itself during a discussion of weekend plans, which may lead to a colleague/friend to check out a band with.

And what happens when the work gets to be too much, and you find yourself stuck at the office all day? Isn’t that the beauty of working wherever you choose? What about those giant cultish companies who directly incentivize their employees to spend all waking hours at the office, or even sleep there?

Well, so, you can just leave. If there’s more work to be done, and your company has a VPN, you can catch up on work at home after having a lovely dinner at a reasonable hour with your significant other. I’ve come to realize (again) the importance of balance - not necessarily the lofty, unattainable “work/life balance” construct of 9-5, but finding a personal balance where I’m challenging myself and working hard, but not burning myself out and still finding time to reflect and find fulfillment elsewhere in my life.

Certain parts of the tech/startup industry paint office culture as a thing of the past, rendered unnecessary by new collaboration technology. Fully-distributed organizations are popping up everywhere, promising uber flexibility and balance. I admire these companies’ ability to embrace technology to try and bring more happiness to their employees - though it is certainly not perfect either. Remember that distributed companies (or remote work at all) is a fairly new concept, far from perfected by any one organization - and the larger the company is that you work for, the harder it is to adapt the necessary processes and technology to enable that flexibility.

All in all? I certainly don’t hate everything. My commute is sometimes frustrating, as can be the work, but that’s part of dealing with everyday life. I genuinely like quite a few of my colleagues (both in and outside of work), which after being remote for a while is quite refreshing. And I’ve achieved a balance that, at least for now, I’m happy with.

The question I now find myself asking more frequently is: where does this go? Do I advance up the food chain of a strong brand with its corporate quirks, or do I keep my hand in some things that could result in more personal freedom? What will ultimately make me a better, happier person?

Well, how many licks does it take to get to the center of a Tootsie Pop?