Adventures in remote desktopping, or the obfuscation of ecosystem

I love working on an iPad Pro. It’s the device that I find myself wanting to continually pick up, and the device on which I seem to get the most done – not always finished products, but the best and most fully defined ideas I can usually bring to reality. That goes for many aspects of my life: personal projects to cultivate my relationship with my wife, writing and producing the bulk of songs, writing and communicating and planning product ideas and larger initiatives for my job, writing this blog post.

My job is doing product management which, while a very complex and multi-faceted job, is essentially reading, writing and talking. Hey now – the iPad is amazing for that. I’ve got Slack, Outlook, the Google Suite of apps, my writing and task management apps of choice loaded up, and that makes up about 90% of the job.

The other 10%? Fairly technical stuff locked down to company-owned devices. I’m diagnosing issues with complex operational products, testing features, writing SQL queries, reading code – stuff that would be insane for a large public e-commerce company to leave open.

To do this work, I am effectively locked into a Windows PC. At least it’s a massively souped-up quad core Windows 10 PC, but…it’s a PC. Stuck between the Google and Office ecosystems. Locked down by IT administrators. This PC is a laptop attached to an enormous dock connected to two Dell monitors in a corner of a big room, neither of which I use or maintain a consistent connection to said enormous dock. Because PC laptop keyboards seem to be all-encompassingly awful, I have a separate, wired external keyboard and (also wired) mouse which still hurt my hands to use, just slightly less so than the laptop keyboard.

All to do about 10% of my job. Possibly less on some days.

Meanwhile, the iPad just sits there, next to said collection of heavy, bulky metal objects connected by many thick cables, waiting eagerly for me to return to the other 90% of my job.

I was recently thinking about why I bother using the PC at all. I don’t mean this to undervalue our IT department, but what does it mean to be a primary working machine in the first place? Can I just pretend that my primary work machine is my iPad Pro, and the PC is just a novelty device that I bring in as the big guns?

Or, could I rely on VNC/remote desktop access for the few things I need the PC for? For a long time, I honestly forgot this was a thing: you could access your desktop computer, in its entirety, from another device.

Turns out Microsoft Remote Desktop on iOS isn’t half bad at all – and since my work machine runs Windows 10, it’s all tablet friendly (thanks Surface) and my sensitive work stuff translates nicely to a 10.5” tablet. I can tap to execute a script, or open a Chrome bookmark, or run a POST request in Postman, or…open a 80MB Excel worksheet.

I have three main gripes with this approach, which keeps me occasionally reluctantly returning to my PC:

  • iOS’s stock keyboard doesn’t seem to like unicode quotation marks – ‘ and ‘, but not `’`. I find myself copying-and-pasting quotation marks around SQL queries, which can become annoying.
  • Since Windows uses different conventions for key commands, and you’re accessing Windows via an iPad, sometimes basic key commands are hard to get right. The basics (Select All + Copy + Paste) work fine, but Windows-app-specific ones do not. I sometimes find myself needing to use a combination of hardware keyboard and Microsoft RD’s built-in software keyboard just to reopen a recently closed tab in Chrome-within-Windows.
  • Google Slides and Sheets (not Docs) are pretty terrible on iOS, so I sometimes need to use Remote Desktop for that. It’s sometimes actually more effective than the native app.

Temporary sanity

I’ve drastically undervalued remote desktop access, and now have an even deeper appreciation for both my iPad and Microsoft’s investment in the iOS ecosystem. It is now even easier to do my job from anywhere, even if that job is locked into certain systems and processes for various reasons.

We might have reached Peak Apps

It’s a great time to be a productivity nut. (Note that this post is going to be incredibly first-world-problem-y in nature.)

Since moving to Berlin I’ve had an opportunity to critically review how I work. My job is for the same company and essentially doing the same thing, but I was able to shed some of the burden of direct reports, longstanding internal processes and borderline-political work relationships, and kind of start fresh in a way. My morning routine has gotten more about me – taking time, eating a real breakfast, learning a bit of German via Duolingo, reading news instead of email.

When my mind is feeling nourished, I plan my day with Things 3, moving stuff for this evening to This Evening, comparing my pockets of available time with the number of tasks or projects I need to focus on, and deferring the least important things. I might draft up a few writing ideas or notes for projects in Drafts, some of which get linked to in Things and others that sit in my inbox for when I have a creative thought later.

My bigger idea boards for things that need planning or some kind of structure sit in Trello.

This all works for me quite well… but on some days it feels wrong. Why manage some projects in Things and others in Trello? They’re both really good, but why do I need Things to supposed Get Things Done when Trello can organize my projects with structure and let others collaborate with me?

Collaboration is important, right? But isn’t focus? Trello can do focus really well, I think. But then again, Todoist is also great for focus and collaboration – plus, it can automatically pull in tasks from anywhere via its API. But, Things can kind of do that through its own URL scheme and Mail feature.

GoodTask can do most of the above too – plus it integrates with Reminders, which is great because I can talk to it via Siri and not have to remember to say “using Things” or something very unnatural. Then again, why not just use stock Reminders since I can remind myself about most of the things I need to work on and have it smartly link back to those things? Moleskine Actions also looks really good too, I think. I haven’t even mentioned OmniFocus, because that’s…too much for me right now.

Literally all of these options are totally fine and look, perform and function amazingly. I haven’t even touched the writing, presentation, mind mapping, or spreadsheet apps. My brain hurts.

It’s a weird time to be a productivity nut. Most of the popular apps in most categories are all really, really good. How do you know which one is best? What is best, anyway?

Best for most people? Best for productivity nuts? Best for a married couple? Best for tech company employees? Best for strong female entrepreneurs? Best for stay-at-home dads? Best for digital nomads? Best for you? You’ll probably find a list like this and see roughly the same 10 to 20 apps in a given category, all of which are really, really good.

Navigating this is really hard. Not because the lists of “best apps” are too long or they’re too expensive or hard to find, but they’re just all so good. It takes a long, long time of trying each one out, being wowed by the unique features or design conventions or automation potential or scalability of each one, and having to decide which secret sauce of those is best for you. Apple is sometimes helpful with this, but other times not. I love the new App Store, but when I see a feature focused helping me “Get to Inbox Zero”, I can’t help but laugh at the 15 email clients they recommend for this – as if they’re sneering, “Literally any of these will work, we don’t care, just pick one.” It’s almost lazy.

Not to mention how those apps in a single category connect with the 10-to-20 best apps in a _different_category. I’ve finally decided on sticking to Things, but do I use that in tandem with Drafts? Bear? Ulysses? Apple Notes? Byword? 1Writer? Each of them? Some combination of these? I could use a cocktail of these different apps that basically do the exact same thing, but how much time must I give myself to figure out that perfect Manhattan of writing a few ranty blog posts on an iPad?

I also have to imagine it’s especially hard now to develop an app in the productivity or writing category and not be in this list. Either:

  1. You could copy some design conventions or differentiating functionality of one of those 10–to–20 apps, do some marketing pushes, and eventually be admitted into the wonderful apps club

  2. You could try and determine some feature or use cases that none of these thousands of people figured out already, and take a big gamble

  3. You should just give up and die

To be clear: I don’t think any of this is bad. I find it an interesting time in the world of mobile-first productivity and content creation where the consumer is pretty much always going to be delighted. Developers of that top-tier bucket of apps clearly know what conventions and functionality their consumers want and are willing to listen hard to understand how to best deliver that. The question for the consumer has gone from “what is the best app out there?” to “what is the app or apps that best suit my particular needs at the moment, but also jive perfectly with how I think or what I want to look at?” The second is a much more time-consuming question to ask, I have to imagine, for most people.

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 life1, 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?

  1. Except when I'm testing iOS betas…oops, maybe I should stop doing that.

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.[^1] 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.[^2] 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 center 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 doe

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, fucking 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.[^3]

The production value (or lack thereof?) gives the song its identity, no doubt. Of course, however, 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 awkwardness 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 this ugly.

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

[^1]: Hopefully his estate will start to release more archived material and live footage so the world can experience more of his purple majesty, but considering he apparently never had a will, who knows what will happen.

[^2]: Yeah, I’m late to the game. Sorry, super fans.

[^3]: This is probably the same underlying reason for my affinity for punk music, which I think lines up with my love for Prince.

Google sometimes drops the ball because Google is a massive company

The other day I finally subscribed to Connected, a great consumer tech podcast, and in their most recent episode, Federico rants about the inconsistent feature support across Google’s iOS apps. (He ranted about it 2 months prior, and the rant still stands.) They’ve failed to provide consistent support for now-core iPad features, including support for the iPad Pro’s bigger screen and Split View. How can you write in Google Docs and do research simultaneously without split view?

Not even being sarcastic. I have to imagine it’s really annoying and hard. If I had an iPad Pro, I’d probably agree with him; in fact I’d probably stop using those apps altogether until Google made them work for me. It sucks even more to notice that Google has updated some of their apps with support for these features. But why not the others, arguably the ones that are the most widely used purely in a productivity context?

I was listening to his rant on my way into work – a place of work where I am one of over 4,000 employees. I started thinking about the different projects that are in flight at any given time within my company and reminded myself: I have no idea who is held accountable for some of those projects. Who knows if they have the same priorities that I do? In just nine months at my current company, I’ve had to deal with multiple fits and starts around projects that involved multiple key teams, only to find out that those teams suddenly had to prioritize these same projects completely differently than mine, due to other external factors beyond my control.

Google is an even more massive organization. It has over 10,000 employees working on any number of products or initiatives. There are teams of hundreds dedicated to Google Docs, Google Sheets, Google Drive, even just the different iterations of messaging (Hangouts & Voice & Chat across all platforms). Each of those teams contain different people, each with strengths and weaknesses and a certain propensity to work harder or less hard than others, or even make occasional mistakes. They also may have different priorities, backlogs and possibly even internal politics.

We have to remind ourselves that each of these factors may translate into different results per product. I would bet that Drive (which coincidentally I think is one of the best Google apps on iOS) has a lot more of its core functionality together and had the capacity to fit split-view support into its roadmap shortly after it was announced. Docs (or more specifically, Docs for iOS) is probably run by a different team that still hasn’t been able to prioritize one of these features. Or perhaps they have it built and in a testing phase, but some QA analyst ran into a massive, crippling bug that Spilt View caused in Docs for iOS but was not a problem in the other iOS apps. Maybe there’s another feature they’ve been pushing for that took precedence over Split View or caused a UX problem when rendering on the larger iPad Pro screen.

Remember when Google+ finally got its Material Design update for iOS almost a year after it did for Android, even after people declared it dead? Why does the Google Analytics, one of the most widely used Google business tools, have a terrible iOS app with an outdated icon and no 6+ screen support? When was the last time anyone tried out Google Earth for iOS? Did you even know that Google has a dedicated Street View app separate from Google Maps? Who decided to make that?

These apps are different priorities for different teams under the same friendly Google brand, so we can’t be surprised when their adoption of features or design principles aren’t totally consistent.

Managing a product roadmap is hard. Managing a roadmap for a single product that plays nice with the roadmaps of other products under a single company is exponentially harder. As frustrating as it can be to see individual products under a brand fall behind others, it’s worth reminding ourselves about these difficulties – especially with amazing new features on which we rely in some contexts of our daily lives.

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?

On malaise in tech, or how I learned to find products that embrace true problem-solving

I originally wrote this for the Mathys+Potestio blog, this really cool employment agency based in Portland, Oregon. Here’s the link to the original post.

Apple and Google and Facebook and Microsoft and Amazon.
These are the big 5 in consumer tech, and the most commonly used apps on your phone are probably made by some or all of them. Nobody is going to knock them out of their ivory towers. If you go on any tech blog you will almost certainly find no less than 3 articles in the last week about each of these 5 companies (okay, maybe a few others – but you know which ones they are).

I’m a product manager by day, so I spend a lot of time analyzing and collecting feedback on the products and how they solve real user problems. Part of my job also involves being aware of other products solving similar or other problems, so I read about those products the top tech businesses are working on, as well as new ones via sites like Product Hunt. But this is starting lose its luster for me – as I recently wrote on my own blog, I’m becoming less and less impressed with the true problem solving being done by makers of products. It gets old to read about a new photo sharing app every week – why try and address the growing wealth inequality problems in the US? Or the terribly slow pace of government action? Or even the racket that is the wedding industry (a problem currently near & dear to my heart)?

Turns out I’m not alone in my jadedness, so much so that some are quitting the “tech journalism” beat altogether. If you feel jaded by this stuff too, it’s valid – but, again, I don’t blame anybody in particular. Tech products, and those who make them, have just as much a tendency to follow trends as any other sector of popular culture – social products, smart on-demand services and lists of resources are hot right now, so all the makers are trying to make those things. (Oh god, what if someone builds a social network for on-demand delivery workers?)

Behind all the throwaway social networks and overpriced delivery apps, though, there’s even more people building truly interesting, difference-making things for the world. This is probably not a huge surprise, given the number of charitable organizations, biotech firms and activist groups out there. But hold up – you don’t need to look only at these types of groups to find great, innovative solutions being developed to solve tough social and economic problems. Startups (and even individuals) are building these things, using the same cutting-edge (and overhyped) technology and design and business models you read about on tech blogs. You know those things called “hackathons” that media has portrayed to us as high-energy bro-outs? (Thanks, The Social Network…) These people are actually using those to address social problems with great technology.

In fact, if there is a social, political or economic issue that interests you, there’s probably at least a few startups or products out there aiming to tackle that issue in some way or another in some new way. Here’s just a few products that are solving real problems in critical spaces that are worth checking out (each of which even use some buzz-wordy tech or design concept you might be sick of hearing about!)

Interested in helping out a charity? Compute for Humanity uses your computer to mine cryptocurrencies, then automatically donate the output to charities. I recently installed this on my own Mac and was pleasantly surprised that it required absolutely nothing of the machine or my time, and yet in a few hours I had generated a couple bucks. I’ve generated $22.64 so far, again, for doing literally nothing.

Why is this remarkable? Cryptocurrencies! No work for the end-user! But also real money going to real, unsketchy charitable organizations like Pencils of Promise and GlobalGiving.

Want to help people with disabilities? Be My Eyes is an app that lets you help out a blind person from anywhere. Remember this thing? It got a fair share of journalistic praise a year ago but naturally fell out of the limelight – not for any reason in particular other than that people’s attention moved elsewhere. It’s worth reminding ourselves, however, that this is an app that literally helps blind people see. That in itself is an amazing feat we shouldn’t forget about.

Why is this remarkable? (Sort of) social networking! Unconventional use of the iPhone camera! But also it helps blind people.

Want to be more socially conscious? Archives + Absences is an app that notifies you anytime a cop kills a minority in the US. This is based on real data from The Guardian – it’s not a joke. If you are interested in the struggle of minorities in this country, you should download this app now, if anything to set context for yourself.

Why is this remarkable? The most minimal design ever! Push notifications! But also they’re about actual deaths surrounding a controversial social topic.

Know somebody with substance abuse issues and want to try and help?Addicaid is an app that aims to make drug & alcohol recovery a little more comfortable. You can find recovery groups nearby, get tips, maintain a plan, and evaluate your progress toward recovery, all while completely anonymous if desired.

Why is this remarkable? Material design! But also it helps people with real, crippling problems get a little closer to solving them.

Interest in the problems of America’s legal system? Ravel, Everlaw, Judicata and others aiming to make the practice of law, and lawyers, more affordable. The first two are building tools to help make law firms more efficient in their operations, and the third is aiming to capture the “law genome” to simplify complex legal decisions for lawyers and everyday people. As Judicata says, “Legal research isn’t just about finding needles; it’s about understanding the haystack too.“

Why is this remarkable? Big data! But also, lawyers are really expensive and law firms are incredibly inefficient right now.

Generally interested in major social issues and understanding their impact? SumAll.org, a tech non-profit hellbent on “empowering change makers to maximize their social impact through data.” They build amazing, sometimes-interactive studies on key humanitarian issues including human trafficking, homelessness and the Syrian refugee crisis. Its founder, Dane Atkinson, wanted tech to create a tangible impact for social good, and formed the foundation out of a portion of his social marketing tech company, SumAll (including its technology).

Why is this remarkable? Data science! But also, the topics they’re covering are, like, really bad things.

Products and businesses, when done right, are about solving problems, not chasing ideas. It’s worth reminding ourselves that in the midst of product/maker overload, that there are millions of people making great, incredibly important products, and they’re even publicizing them – they’re just a little bit harder to find.

Product Hunt for abcdefghijklmnopqrstuvwxyz

The other day I came across Telescope, a product that lets anyone launch their own community site, Product Hunt-style. Just when you think you’ve seen too many “Product Hunt for X” sites, someone gives you the ability to generate as many of them as humanly possible.

It’s not inherently a bad or stupid idea, I swear. But every time someone develops some sort of platform that “lets you make your very own X”, I get a little terrified at the implications that platform may have on society – or, more specifically, the silly ideas that the platform enables. If the “Uber for X” mentality gave us things like this, I can’t imagine what a well-marketed “Product Hunt for X” solution gives us.

Because I get bored during my commute sometimes, I came up with a few ideas for Telescope sites that I thought might be good1. Yay for rapid brainstorming!

  • Anxiety Hunt: submit what’s making you anxious at any particular moment; others can upvote the things that they’re also anxious about. Let’s all be upfront about our insecurities, k? (Speaking of which, is Post Secret still a thing?)
  • Bitch Hunter Hunt: Upvote the best lines from the amazing, non-existent movie starring Will Ferrell, Bitch Hunter.
  • Crack Overflow: Stack Overflow, but for people who periodically suffer from plumber’s crack. (What do you post on a site like that? I don’t know, I wear skinny jeans.)
  • Duck Duck Hunt Hunt: post and upvote screenshots and videos of your favorite moments from the classic game, Duck Hunt.
  • Ethan Hunt: Product Hunt for all things Mission: Impossible.
  • Fuck Hunt: Basically, Product Hunt for porn. V2: import the top voted porn images into a live web version of Duck Hunt!
  • Grunt Hunt: Inspired by Eugene Mirman’s I’m Sorry, You’re Welcome, this gem lets users upload and vote on the best interpretations of various sound effects performed by their own speaking voice.
  • Helen Hunt: Product Hunt for all people in the world named Helen. Vote which ones you think are the best! Except Helen Hunt, of course.
  • I Hunt Myself: For the ultimate narcissist, this platform allows you to submit virtually anything you care about and upvote them based on your personal ranking of those things. The twist? You’re the only one who can access your list. And every upvote triggers a little “Me me me!” sound effect.
  • Jerk Hunt: Product Hunt for douchebags. You literally post about a shitty person and something shitty they did, and people agree with you. The worst people are highest voted. We’re terrible people, right?
  • Karma Hunt: Post something good you did for somebody, and people upvote the most charitable acts. Do you get any actual good karma from this? Probably not. It’s mostly self-serving.
  • Luck Hunt: Product Hunt, but if you're the Xth person to upvote something, you win money. THIS IS THE NEXT LEVEL OF FANTASY SPORTS, BABIES.
  • Meta Hunt: Product Hunt for “Product Hunt for X” sites. Product Hunt is sort of already this, but I figure let’s cut out the BS and make a site dedicated to this thing.
  • Nuck Hunt: Same as the aforementioned Fuck Hunt, but for Canadians.
  • Oregon Trail, Telescope Edition: This version of insanity takes the original beloved computer game, The Oregon Trail, and puts every possible scenario in a list. You have a limited number of upvotes and can use them toward rations, game, diseases – literally everything the game has to offer – and the game returns a likeliness of you surviving the Oregon Trail with those decisions. Basically, a way less fun version of the game.
  • Problem Hunt: Upvote actual problems around which people should build products to solve – they can be any problems, large or small. (Disclaimer: this one’s kind of a real idea, and it already existed once as Real Problem Hunt but was shut down – I think this deserves to come back at some point.)
  • Quote Pilot: You know all those sites with huge lists of inspirational quotes? Ever want to make your own soundbyte-y quote? Submit it here and people upvote the most moving ones. Because we need more inspirational quotes every day!
  • Reverse Hunt: Vote for the least cool things. The less votes, the better. Countercultures, unite.
  • Sidetracked: the Game: submit something that distracted you today – anything at all. Other people upvote the things also distracting them. The test: seeing how many of those things you can avoid clicking on. It’s totally a game!
  • Telescope Hunt: Product Hunt for all sites made with the Telescope platform. (No relation to Meta Hunt, of course…)
  • Uber Hunt: Product Hunt for Uber drivers. Or is it Uber for Product Hunt fans? THE WORLD MAY NEVER KNOW!
  • Viral Hunt: Product Hunt, but with auto-sharing upon every upvote. You thought you couldn't post any more content to your followers? Think again!
  • Witch Hunt: Post people you think are witches, and then others can upvote if they agree with you. Then we burn the highest-voted ones at the stake!
  • X for Product Hunt: Post and upvote features for Product Hunt. (This isn't actually that bad of an idea for a feature request tool…?)
  • Yerba Hunté: Upvote the best kinds of maté…?
  • Zoo Hunt: Zoo animals. Which ones are the best? I’m done with this list.
  1. That is, ideas that will probably get made regardless of whether they’re actually good. In fact, most of these are completely ridiculous. But so are people who insist on making their own “hunt” sites for every possible niche they can think of. Yay products! ↩︎

Peak live music, or no more surprises

What do you do when you stop caring about something you used to love?

I moved to Salem, MA and basically stopped actively seeking live music. I still see live music – say, when my girlfriend and I go out to brunch and a jazz band happens to be performing there, or when a once-in-a-lifetime performance in the city happens – but for years I would spend hundreds of dollars almost every month trying to see as many bands as possible. There were so many possibilities, even in “our music scene is dying” Boston – I would frequent Great Scott and Harper’s Ferry/Brighton Music Hall and The Middle East and (begrudgingly) TT the Bear’s (just kidding, RIP).

I don’t think it’s because I’m getting older. I don’t think it’s even because bands aren’t impressing me anymore. I still listen to recorded music constantly and find new bands via blogs and Apple Music and friends’ posts.

I do think saturation has something to do with it. Software is eating the world and the Internet is eating media, and both of these things are eating our ability to be surprised. The barrier to entry for anyone to become a musician is virtually gone, and it’s really easy for anyone with a slight ego to fight for your attention. The barrier to entry to start a blog or generate commentary on said music is also gone, so with every million bands that form, there are 100 million people ready to comment on said bands.

So you have tons of musicians out there, striving to outdo each other with better performances and more inventive production in order to satisfy the even more so-called critics. The caliber of the average musician is so much higher as a result – and every musician is looking to surprise you, the listener-critic, constantly. Every night holds hundreds of amazing shows competing for your time & attention – secret exclusive shows, bizarre live rigs, intense theatrics, warm acoustic sets – all of which are constantly trying to compete for your interest. It’s all amazing…until it’s all the same to you.

And so I’ve become desensitized to the ability to be surprised by live music.

I’ve been meaning to write about being a musician on the North Shore of MA and how live performance here is different than, say, Brooklyn or Cambridge or other major cities with credible music scenes. I wanted to write about the fact that there is a small but lively group of musicians hopping up and down the shore, playing long & extremely entertaining sets in front of small, passionate North Shore crowds at quaint restaurants and bars. I wanted to write about the scene being smaller, thus allowing me to have a shot of regularly performing with a tight-knit group of collaborators.

None of that has actually happened, and that’s on me. But when you struggle to be surprised by anyone else performing, how can you expect to be inspired to surprise others with your own performance?

Goal: by April, have a live acoustic/looper set prepared and book a show. Try it out.

On Macs and focus

I own an iPad, but I really only use it to watch Netflix in bed with my fiancée since my iPhone 6s Plus is just too small enough for both of us to watch simultaneously. Outside of this pretty obvious use case, I’ve struggled to find a purpose for the gorgeous device in my life.

Everywhere I turn, though, I read about another person finding the iPad completely invaluable in their daily lives. It now exceeds the processing power of the average PC; its app ecosystem is generally much cheaper than the PC app ecosystem; it’s “more fun” to use than any device before. A lot of people who write about the iPad suggest that it allows for a level of focus beyond what Macs or PCs can allow.

I call bullshit. Anyone who says the Mac is too distracting has not given the Mac a fair shot since, well, 2 or 3 versions ago of OS X. Apple has made a series of beautiful, powerhouse laptops, build for demanding technical work – that also happen to be incredibly pleasant to use and conducive to focus.

I’m not suggesting that the iPad isn’t a great device – it truly is a pleasure to use. However, so are Macs, and some tech pundits seem to forget this. Efficiency on a Mac isn’t even a question worth asking – sure, you eschew a touch screen for a keyboard & multi-touch trackpad, but the sheer ergonomics of having both the keyboard & trackpad within millimeters of each other compared to jumping between keyboard and screen are staggering. Sometimes you want to lay back and relax, but when you need to work, the Mac wins every time.

The question really is about one’s ability to focus on a single task or project while working on a laptop/desktop computer. Tons of people have written about this. Those same people have tried incessantly for years to justify usage of an iPad for as many possible use cases as possible: blogging, note-taking, long-form writing, designing, music producing, analyzing spreadsheets, chatting with many people at once. I keep asking myself: what’s the goal of being able to do all these things on an iPad, other than attempting to justify my impulse purchase of an iPad?

If the goal is focus, I’ve wanted to try and tame the beast and have my Mac work to my advantage. Basically, a means of avoiding this:

Screen Shot 2016-01-26 at 8.15.04 PM

Hey, guess what? It's really to avoid the above with really minimal effort and discipline. Between the iterative improvements brought to OS X and its huge app ecosystem, it's really easy to make a Mac your portable productivity powerhouse. (Alliteration intentional.) And while the Mac app ecosystem is technically smaller than that of iOS, that has its benefits: less crap to weed through.

I have to give Apple props for identifying the key aspects that make iOS so pleasant to use and employing them in some fashion within OS X. For instance:

Launchpad is a solid app launcher and organizer; after a bit of reorganizing, it effectively replicates the iOS home screen. With Spotlight (or the more powerful Alfred) on top of this, finding and opening an app on a Mac is far quicker than anything performed on an iPad.

Screen Shot 2016-01-16 at 10.03.10 PM

Full-screen mode and Mission Control in El Capitan is arguably an even more elegant app switcher than iOS 9’s. Split screen mode is actually useful on my MacBook Pro unlike the iPad Air 2.

Screen Shot 2016-01-16 at 10.04.08 PM

Automator isn't new or even quite that extensive without mild technical know-how, but Workflow wouldn't be the iOS powerhouse it is without Automator coming first.

Plus, you can enable Do Not Disturb just like an iOS device.

Still having trouble focusing after trying these wonderful solutions? There's apps for that, including two literally called Focus (here and here) – some of which also have iOS counterparts but many of which are Mac exclusives such as:

  • Bartender, a great menu bar cleaner-upper
  • Hazel, an automatic file organizer so you don't have to clean your crap up yourself
  • Alfred, an amazing launcher and workflow tool that allows you to quickly ask a question or start something without pulling yourself away from the task at hand.
  • Ulysses, Byword, 1Writer, ia Writer, or any other number of free/cheap minimal writing apps for writing without distraction

Some of these are real boons to focus, like the first Focus app, which blocks you from accessing distracting websites and replaces them with inspirational quotes. I could argue that this makes the Mac BETTER for focus than the iPad, since you can actually stop Facebook from loading after you impulsively type the "f" into your browser's address bar. Can't really make the impulsive tap on the FB app icon on your iPad less compelling than it already is.


Disclaimer: I use a MacBook Pro with Retina Display, which has a solid state drive and 16GB RAM, so I’m not really ever concerned about my laptop exceeding the performance needs I have. Yes, it came at a higher price point than the average iPad and I purchased it primarily with music creation in mind.

But considering the top-of-the-line iPad Pro is virtually the same price as (and comparable in spec to) the ultrathin MacBook, it ultimately comes down to user preference. I’m here to suggest that while tablets are so fun and exciting, many of the reasons why find tablets so fun and exciting are right there in your average Apple laptop.

As with any tech write-up, this is my opinion, but I’d love your thoughts too. Agree? Disagree? Let me know. Like how I write? I’d love for you to share this post and follow my writing, either here or on Twitter. Thanks!

On Maker Overload, or why I’m okay with not solving all the problems

Following up on this, which was dead on. In the words of indie darling Courtney Barnett, sometimes I (want to) sit and think, and sometimes I just (want to) sit.

I’m a product manager, which means I spend virtually every weekday (and some weekends) doing two things: solving problems and making things happen to ship good, need-fulfilling products. Anyone who does product management can obviously break this up into many more buckets of duties, glorify it, debate its role in larger business culture, whatever – but that’s essentially what we do.

Sometimes I think I want to build something on my own – I wouldn’t be surprised if most PMs also get this urge. Thanks to a handful of tools that now exist, virtually anyone with Internet access and some spare time can build anything in a matter of hours or days. There’s a lot of people who create their own products on their own these days, using free or cheap existing tools, then publish them on sites like Product Hunt and write about them on Medium. When I read all these posts about “makers” making “products,” I react in a few ways.

First, curiosity, then a little bit of envy.

I love that we now have technology and platforms available for anyone to turn some idea into a packaged product in a matter of hours. Some of the problems people have solved are incredibly niche – I would never have thought of them. Sometimes I wish I had.

Then, jealousy-fueled anxiety.

Why aren't I identifying those problems? Why can’t I be making those things? What do those people have that I don't? What do I need in order to build amazing profitable things myself? WHAT AM I DOING WITH MY LIFE??!!?!!?!!!

Then, a ramble.

Hours and hours on Product Hunt. More things made by more people. Curiosity and anxiety on subsequent repeat.

Then, I'm tired.

I burned myself out worrying about other people's problems instead of solving my own or those problems which I care about.

Why did I do that?


We used to have information overload. Then people rebranded this as #content in an attempt to legitimize it. Now, if the content wasn't enough, we're in maker overload. New startups and new people announcing new products being announced almost every hour on the hour. Call it a lovechild of social media and freelancer culture, both powered by the good ol’ Internet – now everyone can have their own voice, so there’s millions more voices, all yelling incessantly over each other for top placement on your Twitter feed. All so you try the hot new products they each built on their own.

What is the impact of all those new products? Sure, it's huge in aggregate – if anything this is proven by how much pundits are talking about Product Hunt. But what value does each individual new solution to a problem have in the scheme of things?

Product management is really all about solving (the right) problems and enabling the people around you to solve them. Some of the "products" I come across solve problems that aren’t relevant to me at all, but because everyone is posting and writing and tweeting and retweeting about them I run into them anyway. Some of these products don’t solve any problem at all – they generate a problem of their own and attempt to solve it, even if the average person didn’t even need to recognize that as a problem in the first place. Some of those products are really just repackaging the exact same #content that other products already contain, only presented in a slightly different way. Just this year there were 50 products launched, all featured on Product Hunt, that repackage existing tools and content that already wasn’t too hard to find with a bit of Googling. Some of them are totally redundant with each other.

I’m not saying this is inherently a problem – after all, competition makes the world go ‘round. But is this really what makers want to be known for?

Maybe so, or more likely those makers are just trying to make some money or followers. This isn't new – companies have been making redundant products for the sake of staying competitive a long time – but now that the Internet has enabled for a product to get noticed and hyped in a matter of hours, there's too much noise to be continuously making products that don't matter in the scheme of things. It only adds to the information overload, except under the guise of something meant to solve a problem – so people who read about this product (especially those who religiously follow communities like Product Hunt) are inclined to take them more seriously than your standard clickbait. When they do, the maker gets noticed for a day, then just like clickbait, it usually gets lost in the ether of the Internet. Some makers then keep trying to optimize their offering and market fit until something sticks.

Perhaps “maker culture” in tech has also gone the way of the pop music industry.


But that’s not necessarily a bad thing. I’m not suggesting that people stop building things for my own sake. Eventually you might happen across a brilliant solution to a truly challenging problem. Making things to satisfy urges or curiosities, make money, or to grow a personal brand is not inherently problematic – it does, however, create envy within others who aren’t sure they have those same needs. Especially when some of the most “popular” of those products made are redundant with each other or debated incessantly as to whether or not they’re dead.

I thought building my own things was what I should be doing with my life, but it turns out all the product overload is toxic for me. I get into a vicious cycle of anxiety and regret and forced ideation around problem spaces that really don't need solutions at that moment. I don’t personally build things constantly to satisfy some inner need, but I also don’t want to build a career out of making things that follow trends.

I solve problems all day, some of which are incredibly rewarding (like those that make my fiancée happy) and some of which are incredibly dull or frustrating (solved typically between the hours of 9am and 5pm, but even those are sometimes challenging and/or rewarding). In a world where an app can launch and die in a matter, and much of the writing about said app is about whether or not it’s actually dead, I don't want to come home every day and keep doing the same thing – it only stresses me out more. My catharsis is writing songs or posts (like this). Sometimes I want to just watch something mindless or live vicariously through someone else.

And that’s probably why I go on Product Hunt for hours on end. Now I understand the appeal of reality television.

I came into 2016 thinking that I wanted to launch a product, and now that I’m understanding myself better in 2016, the less I feel a need to do that. I have a day job, I better satisfy my curiosities via music and writing, and I don’t have any immediately-obvious solutions to problems I care about. It’s more important to me to be with the people I love and be reflecting and thinking about those problems I do want to solve. If you think you need to be launching products for the sake of launching products, take a minute to think about the merits of doing so. Don’t be a maker just because everyone else is.


Did you enjoy reading this? Feel the same way about maker and product overload? Nice. I’d love a like or share if you do, or you can follow me on Twitter. Thanks!

You Won’t Be Successful, Unless This Post Is

You’ve probably seen a ton of #content appearing on your various social media feeds lately offering inspirational stories, Life Hacks and general tips that might make you a better person. It might not, but at least it’s yet another new thing to try at some point in your miserable life-in-need-of-constant-stimulation-and-improvement.

But that’s not what I’m here to talk about.

You clicked on this post because I wrote a highly-targeted, urgent, actionable title that caught your eye. I got you with a trope. You idiot.

I, however, am an influencer. And I would like to influence you. Did you know that the following people employed tactics to lead successful lives?

  • Steve Jobs
  • Mark Zuckerberg
  • Oprah Winfrey
  • Sheryl Sandberg
  • Richard Branson
  • Howard Schultz
  • Warren Buffett
  • George Soros
  • Barack Obama
  • Most of the other writers on Medium

You probably did learn this by reading or hearing about it somewhere else. But I don’t care about that. I want you to think of me and this post next time you think about any of those famous, successful people. I want you to consume my #content and subscribe to my #newsletter and buy my endorsed #products, so I will inject myself into your life wherever and however I can. You will thank me for whatever Life Hack or tactic or change you made to your life, and consuming all that I spew is the first step.

So, to recap:

You are basically a massive failure until you follow all the points I lay out below.

1. Like and recommend this post and all my other Medium posts.

You might have read dozens, even hundreds of tips, posts, articles or even novels about what you can do to improve your life. But before recommending any of those, recommend my juicy content first.

2. Tell all your friends and followers to also like and recommend all my Medium posts.

Write your own content on Medium where you link to this article and generally reference my wise words and/or expertise on a field I totally have credibility writing about.

But what about the other social networks, you might ask? Yeah, share this post there too. It’s just more content for your friends and followers to digest. But it’s content YOU endorsed.

3. Follow me on every possible social media network & channel on which you can find me.

If you’re not on a network…well, get on it, dammit. I may or may not have profiles on the following sites:

  • Facebook
  • Twitter
  • Instagram
  • LinkedIn
  • YouTube
  • Google+
  • Vine
  • Periscope
  • Foursquare
  • SoundCloud
  • Spotify
  • Dribble
  • Behance
  • Product Hunt
  • Medium
  • Github
  • various Slack channels
  • Etsy
  • Ello

When in doubt, assume I have a profile there. Follow and watch me as I grow my following of minions!

4. Click on every paid advertisement you see that has my name and/or face on it.

I’m not just talking about the sponsored posts on BuzzFeed, Medium, etc. that I clearly paid for to get your attention; I’m also talking about Facebook ads. I even have an in at Forbes who hooked me up with advertising there – you know the 3 second ad you see every time you open up a Forbes article? You might start to see me there. Click on me there. I’ll make some money and burn my image into your brain some more.

I also have some sponsored content on ESPN. I don’t even like sports.

But I LOVE developing my brand shamelessly.

5. Subscribe to my newsletter (because of course I have one) and read it, every single time you receive it, to completion.

Because I know how much you love and value every single email in your fucking inbox. You might already be subscribed to the newsletters of various other writers, marketers and influencers – so what’s another?

Also make sure to click every link in the email several times.

Me, me, me. This is all about me, and not at all about you or your inbox or your attention span.

6. Praise my success with me.

Once this post and my various social profiles reach a certain amount of attention, I will write about it. I will convey to the world how I did it, how you helped me, and what my next steps are going to be.

Then, you can read that and repeat the 6 steps I’ve laid out in this post.


Did you like what you just read? Have you not followed me yet on all my social media channels? If not, it is the single most important thing you can do as a living, breathing adult. Click on this link and this link and that link, and maybe this link too.

Content content content content content content content content content content content content content content content.


Special thanks to all the other digital marketers and social media people who made this satire possible! Sorry, I got frustrated this week with #content. This is not representative of ALL inspirational writing, just a li’l joke about that writing which is dishonest, contrived and/or pandering for the sake of marketability.

Also, sorry that I have to make that clear as to not inadvertently offend anyone.

On “pop writing”

I’m gonna repeat the chorus, and I’m gonna sing it ’til I’m blue in the face

This is a note in response to various posts written on Medium in the last few weeks: one of which was effectively a ripoff another, one of which brought up the fairly obvious point that top content producers (by means of likes & shares, not quality, which is subjective) might simply rip each other off, and a final one which brought to light the inherent problem with all of this.

The problem described isn’t specific to Medium: virtually all written nonfiction on the Internet that gets clicked on by the masses is specifically meant to get clicked on by the masses. A great subset of writers on Medium are no different. Original, interesting writing gets shoved into obscurity while the majority of readers see these repetitive listicles, hollow advice columns and “thought pieces” about Startups, Wanderlust and Life Hacking – because that’s what people appear to want to read. The numbers show it.

I’m fine with that, sure, in small doses. These days, you need some positive motivation to deal with the shitstorm mess that is modern reality. But after a while, as Ben Belser suggests, it gets old. Thousands of “influencers” circlejerking on hearts and fuzzies to promote themselves without giving a shit about what they’re actually saying, robbing the Internet of its soul.

I realized something the other day: Isn't this basically the same as pop music?

Hundreds of thousands of songwriters, composers and performers over generations, mostly working within the same general realm of tonality, mostly attempting to portray the same general emotions and ideas, oftentimes even ripping each other off for the sake of marketability. There are millions of blog posts, ironically enough, about how to do this.

Think about it: all of the most popular songs in the US right now can be confined to a tiny number of styles (hip hop, synth pop, country, with a few rock hits and retro throwbacks). Almost all of these songs are about the following: love, sex, drugs, partying, loneliness, angst. Many even feature the same ideas (emotional or musical) or even the same artists (looking at you, Tay Swift). There are incredibly few exceptions to this rule in the past 15 years – nu metal was an incredibly dumb angry fad, but even Limp Bizkit’s lyrics largely stayed within the confines of the aforementioned 6 topics.

How is this any different from going on Medium one morning and seeing virtually the exact same blog posts you saw 2 weeks prior? The posts are obviously not the same – maybe a different author, a different sponsor, a different tip to make you fitter, happier, more productive – but they're largely interchangeable. Sometimes they are even virtually the same. Like pop music.

So I’ve started to call the majority of what Medium feeds me something else: pop writing. Marketable, interchangeable writing to satisfy the masses. Blogs (at least the most popular ones on Medium) are no longer personal or honest or catering to a particular interest – their sole purpose is to maximize the marketability of the writer’s brand. Not unlike any top 40 artist, CamMi Pham (whose writing and general vibe mostly infuriate me) has a carefully curated personal brand, which draws elements from positivity-pumping wellness and advice writing (and sometimes, directly from other writers). She’s trying to be the Tay Swift of your Medium feed. This fine – millions of people love Taylor Swift, and thousands of people love CamMi Pham’s deliberate, speech-like writing on learning and unlearning and bettering oneself.

You want to figure out how her written brand works? It’s pretty simple, actually.

Come up with a really fucking edgy, attention-grabbing title.

Start with some one-sentence paragraphs.

Write increasingly powerful and emotional statements in those paragraphs.

Maybe a sentence implying initial self-doubt.

Then throw out a big initial thesis.

Usually in bold or headline style.

Then repeat that thesis verbatim, followed by a supporting reason.

The repeat that thesis verbatim again, with further reasons.

What about this other reason? No need to worry, because here’s that thesis again. With another supporting reason.

And that is the thesis, verbatim once more.


Pure, unadulterated crap.


King Crimson (which most people probably know, sadly, from when Kanye West sampled them) have this great song called “Happy With What You Have To Be Happy With” which is basically a brilliant exercise in hollow meta-songwriting. Most of the lyrics discuss the structure of the song itself:

And when I have some words

this is the way I’ll sing

through a distortion box

to make them menacing

It makes for a great commentary on the cookie-cutter nature of pop music construction – there are tropes that one can follow to clearly evoke some kind of emotional response, so we exploit them for maximum feeling. Adrian Belew (the singer) clearly describes the section of the song, what emotion must be evoked within it, and how he intends to portray that emotion; by the time he’s in the second chorus, he’s made it clear the song itself has no meaning: “I’ll brew another pot / of ambiguity.” The bridge, “you have to be happy with what you have to be happy with,” just reinforces that – it’s a nothing statement, weirdly urgent but pointless, endlessly repeating like the advice pieces on my Medium top feed.

(Ironically, that song was written music-first, and the lyrics were thrown in last minute as placeholder. Do you think Adrian Belew cares about what I think the song means? He’s not even making pop music.)

Like how pop music leverages chord progressions and romantic/lonely/excited feelings, Pop Writing leverages the nurturing nature of self-help, the inspiring nature of startup culture & life disruption, pandering political fluff and a few other obvious topics. Let’s call them “subgenres.” Each subgenre, and some artists within that subgenre, have particular conventions that are proven to be more effective than others. It’s already obvious that clickbait article titles is a common theme among all subgenres of pop writing. Some others: pick an icon and find an obscure fact about him or her; pick a bad quality about yourself and gradually turn it good; pander to the founders of an amazing product; respond to that pandering by shitting on said product; give advice to the most blogged-about professionals.

Like how pop music is hard to pigeonhole by conventions but easy to pick out, pop writing is hard to pigeonhole by topic to easy to pick out. One can easily pick up on the writing style of a blogger and exploit it for their own gain. Just pick a topic (even if it’s been beaten to death), read a few popular articles on that topic and pick up on the sentence and paragraph structure. Write a few test-drive articles to hone your skill, and then start marketing your brand. You’re basically doing what Taylor Swift did when she decided she wanted to move into pop music – developing your brand to reach a new audience.

If that’s what you feel like doing with your spare time, weirdo.

Medium is going the way of the music industry, but that's fine.

Nothing should stop CamMi Pham from writing like she does. Medium definitely shouldn’t stop her. That's the free market blogging economy at work. Instead, let's just call it what it is: happy, cookie-cutter, highly targeted pop blogging that will gain her new followers. The market demands it.

The problem seems to ultimately lie in the writer’s convictions. Yann Girard might be more genuine in his writing, but he might not be. Someone writing about a life tip they just discovered might genuinely be so excited about it that they’re compelled to share it with the world. S/he might also be plagiarizing someone else. Who knows?

Maybe the problem ultimately lies in the newfound stigma for content marketing and “social influencers” – people who are paid to get clicks and followers, and thus the honesty of their writing is instantly called into question. Maybe these people could rebrand themselves to appear more honest. CamMi Pham is unapologetic – she admits to being a total fraud and attempts to justify it (within her standard writing convention, of course). Yes, she might be encouraging young writers to steal ideas from others and develop a contrived style of writing that eschews honesty for marketability – but again, if that’s what people want to read, then more power to the writers.

For those who don’t like it: welcome to the beginnings of literary snobbery. Three immediate suggestions for you:

  1. If you don't like pop writing, simply don't read it. Just as I usually avoid the Top 40 like the plague, stop reading the Top Posts on Medium and find writing you like via other means: use Medium's tags, start curating who you follow, or look elsewhere entirely.
  2. If you think Medium isn’t listening and want to help out writers you care about, start your own subculture. Radio failed to capture many niche music genres and scenes, so music blogs popped up to try and promote music in those niches. Maybe fans of certain types of writing will subscribe to a blog or network that heavily caters to a certain niche of fiction or nonfiction. There doesn’t need to be one blogging platform.
  3. If you do genuinely have some honest advice or learnings to share with the world, do so genuinely. Please refrain from marketing tropes, because people can see through that shit. Tell the world what you know, how you feel about it, and if you pulled it from somewhere else, be honest about it. I love reading Jason Fried’s posts for this reason – he’s honest, witty and daring and has legitimate reason & experience to pull off all three.

I’m going to tag this post and hope it gets some likes and shares (which, by the way, you should do if you think it’s useful). It probably won’t, though, because I’m not a digital influencer with 500+ followers on Medium.

Yet.

Because I’ll keep trying.

Maybe I should read one of those “Top 10 Ways to Find Success on Medium” posts for help.

Earthside reinvigorated my faith in prog, and took me back to my roots

Music that challenged me in 2015, part two

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As part of my reflection on the music that inspired me in 2015, I started writing a bit about those albums and songs that will largely be overlooked by Big Music – but are still ambitious, challenging and exceedingly interesting. In this post, I’ll discuss the first progressive metal album I’ve listened to in years, Earthside’s A Dream In Static, and why this album is particularly important to me.

Why do you listen to music? Most people seem to just to get through their sad, meaningless existence – whether that means mellowing out to a pleasant acoustic ditty or raging to a club banger or some good punk rock. But regardless of what genre or why, you put music on in the background to feel something.

TLDR: If you want to not just feel something, but feel it with a level of intensity you might not have before while listening to music, you should listen to A Dream in Static by Earthside.

I grew up listening to mostly angry music. My parents didn’t push this upon me – in fact, they didn’t really make me angry at all or neglect me or listen to any angry music themselves – all I had was radio and my MTV. I distinctly remember the first time I saw the video for Eve 6’s “Inside Out” and having the silly cathartic moment that every young boy feels when he first witnesses ANGST. I started headbanging. I was then running around my parents’ living room, not dancing, but slamming my feet into the ground, punching the air in miserable joy. I wasn’t a sad or angry kid, but I think this (and a few other songs) stuck with me in such a way that dark and angry music resonated with me more so than any other.

When I first heard Tool’s “Schism” in 2001, I had a similar standout moment – the video, but more importantly the music, shocked me. Rock music could not only let me express my (misplaced) anger, but also make me feel awe, dread, all those existential feelings I had never experienced to that point at the ripe young age of 12. It was shortly after this that I learned that Tool was of a group of largely uncategorizable heavy bands, but usually pigeonholed into the genre of “progressive metal” – an overly generalized term for bands who skirt the norms of time & key signature, focus on big topics & bigger sound, and have small but extremely rabid fanbases. I became one of those rabid fans – first of Tool, then of Dream Theater, Porcupine Tree, Ayreon, Opeth and various others. I shared this with my dad who then exposed me to Yes, Pink Floyd and King Crimson, and I became obsessed. I HAD to learn everything about every song, how they all connected, what bizarre alternate realities the songs existed within, how the time signatures within a song related to the purpose of the song itself.

In 2004 I picked up bass guitar and, shortly thereafter, joined a band in high school bent on making powerfully emotive and complex music to try and channel this fascination into something productive. But because we were nerdy teens from suburban Connecticut, we didn’t have a whole lot of actual hardship to channel into powerfully emotive music. Plus, none of us were confident in our ability to write lyrics – so we made dark, edgy, self-indulgent instrumentals with silly names like “Mariachi Massacre” and “The Greatest Wall.” But it was a hell of a lot of fun – and we made some fairly cool music for a bunch of weird teenagers from Connecticut.

Then I went to college, started drinking, got a girlfriend, and landed my first internship – which happened to be in both the music & tech industry. I was around tons of other musical tastes and quickly got tired of the pretentiousness of prog metal. It just wasn’t vibing anymore, man. So I quit that band in late 2008 and tried my hand at some other stuff: a Talking Heads cover band, playing lead guitar in a stoner rock band, trying my hand at writing alone and with other people. To my old band, I said that I didn’t want to write music like that anymore and could not endure the impossible uphill battle that is trying to achieve noteworthiness as a prog metal musician. My tech career was more lucrative and important.

In 2014, that band publicly became Earthside.

earthside-band-photo.jpg


I remember a few years earlier when Jamie (Earthside guitarist and one of my closest friends to this day) sent me a rough cut of “The Closest I’ve Come,” a sprawling instrumental track that I had learned a few years prior when they asked me to fill in on bass for a show. They had finally locked down a permanent bassist in Ryan Griffin and tightened up the composition to the point where it was release-ready. I remember being impressed by my former comrades – an appropriate development of the initial sound we had established as Bushwhack, more focused, “cinematic” and, most importantly, nuanced. There is a specific breakdown roughly 6 minutes into the song in which all instruments abruptly pause – except for a quiet, ominous arpeggiating keyboard line that wisps you out of riffs and into a floating sensation. The guitar levitates with you, occasionally supplementing the keyboards with subtle harmonic feedback. It’s as if you’re being slowly pulled upward toward the cosmos – until drums, bass and guitars suddenly shatter a glass ceiling above you and push you back down to the ground with the most brutal rhythm of the song thus far.

To say that this was representative of the scope of the album they were working on is a gross understatement. Jamie had mentioned they were toying with the idea of guest vocalists, researching string quartets and small orchestras to record with and some producer in Sweden I hadn’t heard of. I largely disregarded all of this – where did they have the money to pull all that off? I certainly didn’t, and I was the one with the lucrative tech career.

But after over almost 7 years of hard work, Earthside finally released a true debut – an 8-track, hour-plus-long catharsis of a debut. It’s sometimes a difficult listen: it’s brutal, it’s morose, it’s jagged and it’s exceedingly triumphant, sometimes all in one track. It begins with the aforementioned “The Closest I’ve Come” as a hint of the journey this album takes, which in the band’s words encapsulates “everything we are as human beings” – which isn’t wrong.

See, the thing with A Dream in Static is that, while it occasionally uses prog-metal clichés in its song titles and lyrics (eg. all the self-actualization stuff, the song title “Entering the Light”), it makes the rare achievement of actually embodying those emotions and ideas in full. “Entering the Light” makes you feel like you’re actually marching toward said light, and then when all instruments are distant except for a quiet string harmony, you feel as if you’ve finally made it – only to discover you’re back where you started, marching again. I haven’t heard another rock song (let alone an instrumental!) that made me contemplate my own mortality like this in years. The scale of this album is enormous, and that’s ignoring the fact that these are still my nerdy friends from high school. Every single performance of every single idea is executed flawlessly – technically near-perfect but still human at its core.

Let’s talk about the 10-minute “single,” “Mob Mentality” – if any song attempts to represent the absurd mess of the state of our country right now, this could be the song that does it. (Ironically, it was recorded in Sweden.) I know this song is deeply personal to Jamie, as he wrote it both as a senior college thesis and as a means to deal with his own confusion of his life’s next steps, in a world where influencers are complicating your own worldview more than ever. Who has any idea what the hell is going on in their own lives and what’s going to happen next? And better yet, how is the persistent influence of others making that anxiety any less overwhelming? The sheer scale that the Moscow Symphony Orchestra and Lajon Witherspoon’s 1 performances bring to this workout of a piece is daunting, but also intensely relatable and satisfying.

There are three key breaks in the piece that make the song work. The first, a deliberate breath of curious air; the second, a sudden dip into playful terror as Lajon sings “and I pray for you to see / I’ve been sheltered by my bliss”. The last break of note occurs with only about 40 seconds remaining, after the song’s final climax has already been hit – it’s the song’s “Oh shit!” moment as the band takes you back to the original melodic idea that began this ride.

Oh, and this is the second track on the album.


There is no particular secret sauce to a progressive rock or metal record; some songwriters devise a complex storyline or overarching concept which may be explored lyrically or within the musical structure itself. However, much of “prog” has fallen into one of two traps: it either falls back on past tropes and stereotypes and, in the process, loses originality and/or emotional weight; or it gets so tightly fused into other genres of music that it’s barely noticeable (read: the first two Coheed & Cambria albums, which I still find excellent). When I was playing prog metal in Bushwhack, we were intensely aware of those tropes – as well as tropes in other styles of music – and tried to turn them upside down and meld them together into odd results. Over time it became less about fun genre-shifting for our own amusement and more about actively trying to bring complex (yet sometimes competing) ideas and finding some kind of emotional synergy. I’m happy that this band continued down this path.

“Skyline” (track 5) probably contains this year’s most awe-inspiring musical idea. As the band explains, about seven minutes in, the song follows 3 rhythmically competing lines (on piano, drums and lead guitar) for nearly a minute, winding around each other like synchronized birds in flight. Then suddenly they all meet and come into rhythmic unison in one of the most joyful, cathartic, nearly orgasmic musical expressions of cosmic scale I’ve heard. Even before this moment, this song dazzles: the song begins with a sudden thud after the quiet march of previous track “Entering the Light” and, after a brief introductory theme, breaks into my 2nd favorite bass line of the year (sorry guys – “King Kunta” wins this one).

Structurally, this album is half vocal tracks and half instrumentals, but each track contains at least one satisfying surprise. The title track, which features Tesseract’s Daniel Tompkins on lead vocals, seems unassuming at first – until its first chorus. I have not heard a more intensely joyful vocal performance in prog than Daniel’s in this song. “Ungrounding” is the one instrumental I haven’t mentioned yet, and while it seems fairly straightforward technical metal at first, there are two elements of this track that once again demonstrate the mastery of composition this band has. First: Frank (keyboardist)’s melodic line – out of context, it honestly sounds like it was lifted from a trance or hip hop track. It’s this fast-moving airy synth that almost works an attempted homage to Lil Wayne’s “Lollipop”. But once placed against the rhythmic complexity of “Ungrounding”, it takes on a whole new character that embraces chaos – what was once intended to put its listeners into a trance has now run amok.

Second: What the first half of “Ungrounding” does to inspire chaos, the second half does to make sense of it. There are feelings of grief, rage and outright fatigue (paired with a downtempo, down-octave version of the original synth melody). I remember first listening to this song and not expecting much beyond the first minute or two, but the second half pulls you back in with force – a testament to Earthside’s ability to truly capture attention and tap into the deepest reaches of your psyche.

The album closes with “Contemplation of the Beautiful,” a nearly-12-minute brooding funeral march; one could argue that it refers to the previous 7 tracks just as much as its subject’s waning sense of self. A Dream in Static does encompass everything we are as human, from the wonder of birth to inevitable death. Its ability to traverse tough, complex emotional ground with focus & grace, and it’s affected the music I find inspiring and even how I approach writing music. It tells a story through music more vividly than most concept albums I’ve heard and has reinvigorated my interest in metal & prog, and I cannot recommend it highly enough to anyone who genuinely wants to feel their emotions heightened by sound.

But more importantly, my friends made this record. Friends whom I have a history with making music and I left to pursue my own path. Part of me wants to be jealous, to question my decisions to pursue tech and solo songwriting; but a much bigger part of me is proud and amazed at these guys. They gave me a reason to once again appreciate my musical foundations and our time together as a band. If anyone reads this and happens to have a friend in a band, I encourage you to give that band an honest listen – they might just surprise you with something great.

  1. Yes, Lajon of Sevendust!!! #90s ↩︎

In Defense of Miley Cyrus & Her Dead Petz

Music that challenged me in 2015, part one

I haven’t written a “favorite albums” list in a few years, mostly because I realized that mine were virtually identical to most of those my friends would write up. That’s one of the unfortunate downsides of having friends in the music industry: if a band gets enough hype to be in a Top 10 list, everyone’s talking about that band.

2015 was one of the first years in a while, though, in which a lot of the buzzed-about music was downright ambitious: while there was plenty of crap for the masses to party/drone to, there were also plenty of musicians who stopped giving a fuck about playing nice and made cool, interesting, challenging music. Cases in point: Kendrick Lamar, Bjork’s Vulnicura, “Hotline Bling” and Titus Andronicus’ 90-minute manic depression rock opera, just to start.

I felt inspired by all this and had one of the more prolific years of writing music I’ve ever had. Some of the music I found most challenging and inspiring, though, was reviled, dismissed, or missed entirely by mainstream music journalism. I’d like to spend some time reflecting on the hidden genius of those songs and albums.

Let’s start with a doozy: Miley Cyrus and her Dead Petz, released via SoundCloud & VMA surprise in August.

I don’t dance much, but two songs this year made me start dancing more than any other: “King Kunta,” for obvious reasons, and Miley Cyrus’ “Slab of Butter (Scorpion).”

Don’t ask me why. I can’t explain it. But that damn bouncy synth texture paired with a fuzz bass made for my downtempo jam of 2015, and I’m not mad about it. I’m only mad when it ends, and then after 45 seconds of Miley talking about how drunk she is, the beat comes back in the form of a fun diss track called “I Forgive Yiew” (sic, but who cares? Miley sure doesn’t). The slow bounce continues for another 3 minutes, and it’s kind of glorious.

The next song, “I Get So Scared,” haunted the shit out of me when I first heard it. It still does, which is a weird thing to digest given that this is BASICALLY HANNAH MONTANA telling me that “they say love grows / but I’ve only seen it die.” After that happens, I find mellow euphoria in “Lighter,” a highly underrated 80s throwback.

People HATED this album. I don’t. It’s weird and sprawling and usually inappropriate, but every time I come back to it, I find another nugget of something charming, dark or downright beautiful. “I Get So Scared” is one of those nuggets.

Sure, it starts with the silly “Dooo It!”, but immediately after you get 2 solid ballads in “Karen Don’t Be Sad” and “The Floyd Song.” For every stupid track on this album, you get multiple gems. Sure, “Milky Milky Milk” is probably a song about lactating, but it has one of the coolest beats of the year. Sure, Miley cries when singing about Pablow her dead blowfish, but you can’t fault her for expressing some real emotion in a song. The 6-song run of “Cyrus Skies” to “Lighter” is pretty fantastic, and could make for an excellent psych-pop EP in itself.

I do think Miley brought some of the bad rap and flat-out dismissal upon herself – the “complete, full-metal DGAF” approach to album structure and focus, plus the fact that she made this album outside of her recording contract, lends the album to be taken both less seriously and more like it’s trying be taken seriously. Most of the negative or apathetic critical reaction has been based on the assumption that this album should be interpreted as higher-concept than it probably should be. And to those critics, it disappoints as a high-concept pet project.

But why should we treat Dead Petz as anything beyond what it is at face value? It’s a long, sprawling collection of songs covering several topics, some of which are very silly. Nobody gave Prince any flack about that when 1999 came out and contained a song about vinegar strokes and another one with 2 uncomfortable minutes of orgasm sounds. Why should Miley Cyrus be dismissed for calling a song “Bang Me Box” when Nicki Minaj can release a song glorifying her own ass, or a song about a girl who makes crack cocaine became one of the top hits of the year? (Oh and remember when a song about shooting up a school became a pop hit? Great job, music industry.) Dead Petz doesn’t need to be anything more than it is, and critics shouldn’t dismiss it because it doesn’t reach their impossibly high standards of long, ambitious works that break political or spiritual ground. It’s as if critics are no longer willing to let their subjects just unwind and not be taken too seriously.

If anything, this album disappoints me because it makes me wonder how it would have been accepted if a few throwaway tracks were removed and it was a bit more polished. If “Fuckin’ Fucked Up” (which should not be treated as anything more than an interlude) was removed from the track listing and was attached to “BB Talk” as a prelude, would people use it as an excuse to dismiss the album? “Something About Space Dude” is effectively a coda to “The Floyd Song” – what if Miley positioned these two separate tracks as a single 8-minute space rock epic, like what JT did with some of his solo material?

For those who want to give this album a second chance but can’t deal with the full 23 tracks, I propose a revised Dead Petz track listing, which is only an hour long:

  1. Dooo It! <— only because nothing else really works as an opener
  2. Karen, Don’t Be Sad
  3. The Floyd Song (Sunrise) w/ optional coda: Something About Space Dude
  4. Space Boots
  5. BB Talk
  6. Milky Milky Milk
  7. Cyrus Skies
  8. Slab of Butter (Scorpion) w/ optional coda: I’m So Drunk
  9. Lighter
  10. I Get So Scared
  11. I Forgive Yiew
  12. 1 Sun
  13. Pablow The Blowfish
  14. Miley Tibetan Bowlzzz (bonus track)

It’s really hard to take Miley Cyrus seriously, and that’s okay. Bizarrely enough, the thing that convinced me to have respect for her is the album in which she takes herself the least seriously. You should give this album a chance if you didn’t yet this year.

—-

Oh, and lastly, I put out an EP too, but it’s probably not on anyone’s best-of lists because I barely promoted it. Check it out, though! It’s fun.

Apple Music Connect, the experiment

Federico Viticci of MacStories wrote this yesterday and it got me thinking about Apple Music Connect, which I’ve started to check daily:

The responses to this tweet are varied, but they generally echo the sentiment that I've been seeing in music industry writing: it's largely doomed to fail. The UX is somewhat crap (not denying this) and the positioning is unclear (also not denying this). I'm sure Apple will work on this over time, but it's hard to convert users if they start off with a bad first impression (hey, iTunes Ping / Tidal / any other music network that fails to catch on).

But we shouldn't be surprised that Apple Music Connect is adopting slowly. For major artists, their labels (or the artists themselves) have already bought into another streaming service – most of the majors into Spotify, and the dozen-or-so upper-echelon folks who co-sponsored Tidal – so why should we expect them to suddenly release a single on Apple Music Connect for the sake of their fans? Fans by nature are rabid, so they’ll follow you to whichever network you choose (this is why Tidal didn’t die on arrival). What’s the incentive for Kanye West to post his new stuff on Apple Music?

SoundCloud is in a weird spot in that it has the adoption of millions (including Europe and Asia, perhaps most importantly), but isn't necessarily tied directly to labels. In other words, there’s no incentive for Kanye West to NOT post new music on SoundCloud – no conflict of interest, no problem. That said, the network's moves to partner with brands is probably causing other strings to pull artists toward it. The general public will probably never know the full scope of it, but it’s worth assuming that major artists are probably picking their music networks of choice very strategically.

But Apple Music (and more specifically, Connect) is not going to pick up like this, with the exception of a few possible artists with existing partnerships with Apple (read: Trent Reznor, Dr. Dre, Adele & Coldplay)1. And I’m fine with that: it’s not done. Apple admitted that they still have work to do. Anyone who’s tried to build or work at a startup knows the difficulty in launching a good MVP quickly. While we instinctively seem to hold Apple to a higher standard given their massive stack of cash, you can’t blame them for putting out a brand-new streaming music service and wanting to iterate & experiment. I’ll be a contrarian: I love the idea of integrating streaming & social music discovery within the existing music player. Why not talk about music in the same app that you listen to music? Sure, it may look cluttered due to “bad UX” and purposeless due to low adoption, but it’s an interesting approach at trying to bring the relationship between artist and listener closer to the music itself that establishes that relationship in the first place. That’s a pretty massive and difficult concept to get right, so I can’t be surprised that it’s a little messy the first go-around.

Any new, minimum-viable product requires iteration and experimentation. No matter what they say in PR announcements, Apple has to be trying to experiment with Connect. You can’t write a music product off immediately when artists don’t flock to it immediately; great things take time to get right.

  1. Woah, rhymes. ↩︎

The problem of task managers

Wunderlist, Trello, Todoist, OmniFocus. 2do. Things. I have to imagine that most smartphone users haven’t even heard of these apps. That's probably why there's such an apparent subculture around each one. The average person will never break into the most beloved apps, and those who do will defend it to no end.

So why don’t so many people, who presumably have things they need to do in their lives, use one of these tools? For all the people that do try a project management tool, why do so many underutilize them?

Everyone has a smartphone, and most of them probably use stock functionality (read: Reminders & Calendar) to keep track of their daily lives on that smartphone. However, Reminders rarely has accountability – what if you forget to set a reminder time? What if you miss the location-specific notification by the time you’ve left? What if some to-dos are dependent on others and you can’t check them off the list until some other thing you neglected gets done?

Are the to-dos I’m getting reminded about even a good use of my time right now?

What about the big important complicated things I want to do?

How do I even break those things down into the little to-dos to put in my list?

What does that mean to me in the big picture?

The average person doesn’t want to (and almost certainly can’t) think through all that stuff, even though they potentially have implications on their daily lives.

This conundrum, in the workplace, is basically why project and product managers exist. Product managers help to figure out the right things to focus on and why; project managers make sure they happen so you, Mr. Stakeholder Guy don’t have to worry about all the little details.

Personal assistant apps exist, even virtual ones, to remind you of upcoming meetings and tasks – so why haven’t we developed a “personal product manager” that takes your big goals in life and helps you break them down and focus on the most achievable pieces of said goal?

I think about the big things that I want to eventually do in my life – get married, build a company, buy a house, be a notable musician, other things – there’s a ton of knowledge of what to do to make those things happen on the Internet. But parsing all that information is a nightmare – you’re basically relegated to Google searching or starting with blogs/resources you trust and vetting the content endlessly until you end up with a series of tasks, which may or may not be in order, prioritized or even possible. Then, you have friends and/or family as a resource, which may contradict your online findings (or even each other). I don’t even want to think about the difference between my dad’s opinion on starting a business compared to my previous employer.

Productivity apps can’t do this thinking; it’s not what they’re designed to do. 2do, one of my favorites, requires a whole lot of task creation and organization in order to be truly useful. and People have said that about Evernote, too. Trello is great for visualizing projects in a board format, but it doesn't tell you what should populate that board and what of that stuff needs to get done in order to make BIG AMAZING GOAL X happen. (That's probably why they've started collecting and sharing sample boards for various use cases.) The thought process around focusing the idea into discrete pieces hasn't been productized for personal lives.

I wonder if this is why productivity apps aren't ubiquitous – because they exist to humor the details of lives instead of boiling them down to what’s important.

Share that you’re still learning (because everyone else is, too)

The Internet is amazing, and Twitter is amazing. I know someone just wrote a post about how Twitter is dying, but the communities of people who are using it in the correct, intended way are great.

I bring this up because earlier today, for the first time, I tweeted something that sort of went viral. It didn’t actually go viral (the numbers were clearly not large enough to be considered viral), but for the first time:

  • I shared something I thought could be valuable to others
  • it got picked up by an influencer (thanks, folks at Product Hunt!) who similarly thought it was valuable
  • it then got picked up by several dozen others (58 favorites and 13 retweets, to be specific)
  • I was thanked by many people for sharing, despite not knowing these people at all

Again: chump change in the world of Twitter, but it still made me happy. Happy that I got some attention, but even happier because I provided value to some people I don’t even know. This all happened because I shared the fact that I’m still learning.

It’s been written ad nauseum that startup/tech journalism has a tendency to focus on successes. I had assumed that tech thought leaders and sites like Product Hunt only cared about actual products and results; I figured I’d learn to code so that I could eventually build products that changed people’s lives and brought me financial stability and fulfillment on my own terms. The reality is that I’m probably years (at best) away from pulling this off.

But starting somewhere is important, and sharing this (even if you’re still at the bottom of the proverbial totem pole) is worth doing. There’s millions of people trying to build their own products and know as little or less than you do, so why not make it known? You may be able to help each other out, bounce good ideas, test each other’s works in progress or even make some friends in the process. Now that I’m public about my learning how to make iOS apps, I’ve got a little more community around me, and while the path forward still isn’t totally clear, it feels a little clearer now.

Thanks Product Hunt and everyone who liked what I had to share!

It’s not obsessive-compulsive

Every day when I get home from work, I walk in the door, kiss my girlfriend Alicia and start organizing things. If it’s Monday, I take the trash and recycling out to the street and line up all our bins neatly in a row. Otherwise I put my keys on the hook, my wallet & sunglasses in a tray next to said hook, pick up the small pile of bags, jackets and/or shoes that Alicia leaves by the door and put each item in its respective closet or corner; then as she starts cooking I tidy up the non-junk mail we received that day, throw the rest into recycling, wash my coffee mug out in the sink, wash her mug out, review the state of the dishwasher. Next I'm washing dishes as she uses them to cook our dinner; it looks like a Charlie Chaplin assembly line if we have the right background music playing.

We eat. Sometimes in front of the TV, sometimes at our brand-new first-owned dining table. I compulsively pick up the dishes to go wash them, sometimes regrettably before she's even done eating her dinner. The dishwasher is full, so I might as well run it. The laundry hamper is full, and I'm getting low on t-shirts to wear to work – should probably do a load.

By the time I start relaxing, it’s either too late to play any music (might wake up the neighbors) or I burnt myself out just tidying up the place. But for me, having control over my house grants me the calm I need to relax & think creatively. It’s not obsessive-compulsive (maybe it is? Who knows/cares); but it’s a mental exercise that keeps me proud of what I’ve got around me. Most of us go through days (even weekends) without thinking much at all – at work, at social events (which take less thought than the decision whether to even go), even when trying to write something (yeah, that's a stab at lazy blogging conventions, so what?).

For a long time I tried to force creativity, dedicating whole evenings in front of a MIDI keyboard trying to compose – but instead of writing any great melodies, I ended up lazily repeating the same riff I’d written years prior over and over for 3 hours with nothing new or different. My head was in the wrong space during those forced moments; obsessively organizing my home life seems to correct that. I’ve learned to love the process, even though it's sort of compulsive by now.

Also, Alicia loves not having to do dishes or laundry, so win-win.