An extremely good problem to have

I just ended my one-year expat assignment for my company. I’m back in the US, most likely for good — so long, massive weekend farmer’s markets and cheap healthcare; hello political malaise and smartphone convenience.

While I was in Berlin, my job was very specific to the European market and required a deep embedding into European office culture. A lot of the standard corporate tropes apply — abundant meetings, open office environment, good-and-bad stakeholders to manage — but knowing how to navigate the interpersonal relationships and cultural nuances of an office is best done by immersing oneself in that office. Doing the same job from remote is, in a 8,000+ person company, difficult to sustain.

So now I’m in transition. Still at the same company, but looking for something to take on next as I phase out of my current responsibilities.

This has led to a very interesting phenomenon: a whole lot of teams seem to want me. I have spent roughly 30% of my last week simply meeting new people and learning about other problem spaces going on within the company, to see if they are interesting and impactful for me to take on.

While in many parts of both the US and the larger world people are constantly finding themselves out of work, struggling to make end’s meet, I’m having no less than 6 unique jobs thrown at me (disclaimer: all at the same company) with a crazy amount of enthusiasm.

This is an extremely good problem to have, and something I have weird feelings about.

  • I don’t love saying “no” despite having to do this a lot in my job. This is that same problem, but at a meta-level to product management — for the roles I don’t take, it’s: “Sorry, I don’t find your problem interesting enough to take a full-time salaried position to go solve.”
  • I’ve underestimated how many interesting product management problems there are at a Big E-Commerce Company. It calls into question why I spent over 3 years in largely the same space — doing different things, in different markets (and spending a full year living in a different market). But could I have been even happier by looking for these opportunities earlier on? Why aren’t some departments more proactive about showcasing their problems & solutions to attract people?
  • How firm of a decision do I really _need_ to make? If I pick a role that I like on paper and end up disliking, how easy is it to recall these same opportunities I’m currently being presented with?
  • Consider the bargaining-chip aspects of my position. If so many people want me, can I make them fight for me? How much of _that_ am I willing to push for, as opposed to simply being happy in my next position?

I realize these are extremely first-world questions to be asking. I am in an amazing position. But decisions are hard. And while it’s probably all going to be fine regardless of which path I take, I desperately want it all to be fine.

Originally published at tonedeafcolorblind.com on August 26, 2018.

Gear / Hyperportability

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


Hardware

Most of the time I’m doing things on an iPad Pro 10.5″ (256GB) or an iPhone 7 Plus in Slate Black (also 256GB).
 Heavy music production, code tinkering and design gets done on a late 2013 MacBook Pro with retina display, which I share with my wife. I also wear an Apple Watch Series 3 (GPS only, suckers).

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

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

Software

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

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

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


Originally published at tonedeafcolorblind.com on July 15, 2018.

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.

Originally published at tonedeafcolorblind.com on May 22, 2018.

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.


Originally published at tonedeafcolorblind.com on April 28, 2018.

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.


Originally published at tonedeafcolorblind.com on September 12, 2016.

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?

Originally published at tonedeafcolorblind.com on August 31, 2016.

Creative work on an iPad (via Mathys + Potestio)

Instead of doing a bunch more experimenting-with-iPad posts, I was asked to do a write-up on using iPad in a bunch of creative contexts, and this is what resulted. I’m having a lot more fun lately writing and tinkering on my iPad, and now that I’ve moved to a new place with some nice scenery, I’ll probably be spending less spare time at a desk and more out in nature — for which the iPad is perfect.

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.

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 are 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.


Originally published at tonedeafcolorblind.com on May 4, 2016.

A small set of apps to keep me creative

There’s something I keep having to remind myself: no matter how little time I have to put into art, I’m still an artist.

Still an artist, still making art. Music’s my medium of choice. Finding time to work on it is hard though, between wedding planning, an increasingly-demanding day job, other side projects — when can I play or write some music, dammit?

Short, obvious answer: block my time like nobody’s business. That at least gets me time dedicated to working on the things I want to be working on. Once I’m there, how can I explore purely creative ideas and save them when my brain is full of all this other stuff? Equally short, equally obvious answer: technology helps me. But how?

I used to think that Evernote should be my catch-all for organizing my stuff to stay focused: important notes, snippets, ideas, lyrics, receipts, anything possibly necessary to retrieve in the future. Tagging and shortcuts, stacks o’ notebooks, so much control. I tried storing my lyrics, song ideas, high level album cycle plans, even task lists and reminders in there — but, as others have noted, I ended up overwhelmed anytime I even attempted to find something in the depths of Evernote’s robust (to a fault) categorization system. I had access to too many things all the time — I had to remember which tags corresponded to what in my bizarre system of organization, not to mention the hours blown trying to establish the system in the first place.

Then I tried 2Do for a while — I figured that if I could abstract my tasks out of their various places into a single, meticulously organized place, I could get to all the other pertinent content via links. 2Do’s various features are great — but again I felt overwhelmed, like I was spending more time organizing my ideas than actually executing on them.

I realized that these approaches contradicted my way of thinking through my various blurbs of information when I need them.

So I worked out a new system. Here’s what my core criteria was for this:

  • I cannot put all my things in one place, due to the sheer overwhelming of having to parse through it all each time.
  • Centralize the blurbs in the app best for those blurbs. For instance, the app that gets me quickest to my notes is the best one for the most important or most frequently used notes.
  • More abstract ideas that require gestation and iteration don’t require as quick access, but I need the flexibility to adjust, merge, rearrange those notes as my ideas come to fruition.
  • Markdown is amazing, but some ideas may require sketching, images, etc. so I can’t limit myself to just text.
  • I need this system to play nice with day-job work and creative work.

Turns out I was able to devise a system that works for me quite well — and it’s not far off from what others have written about recently. Here’s a shortlist of the apps I use in this system:

Reminders.app: my high-level starting point

Apple’s stock Reminders is what holds all my shit together. I tried using so many different task management apps and realized that the overcomplexity of these apps was what caused all my wasted time and lost focus in the first place. With iOS 9 and El Capitan, I can now save virtually anything to a Reminders list and have direct access to that thing, regardless of where it lives. I can even dump tasks straight into a list thanks to 3D Touch.

Disclaimer: A big reason why I went with Reminders was due to iOS Exchange integration. We use Exchange at my work, whose Tasks feature I rely on to organize to-dos each day. Having access to them on my phone is invaluable, and while I loved 2Do for my personal projects, I haven’t found a great iOS task manager that handles Exchange tasks.

I have a few key lists I rely on:

  • I created an “Inbox” list that functions as my collector of tasks. I rely on Siri and share extensions to put everything into this list, and I sort out as needed later.
  • I have a list for each major focus area: Wayfair (via Exchange), Sophomores, wedding planning, writing topics (for the blogs I contribute to), etc. I also have a generic “big goals” list for personal bucket-list items (starting a podcast, writing a book, etc.)
  • I also have a few lists for other things to reference: stuff to buy (Shopping), stuff to watch/listen (Media), stuff to take care of around the house (the Family list I share with Alicia).
  • I rely on Smart Reminders to link to the given Note, Trello board, Ulysses sheet, or whatever else is pertinent to the given task. These were pretty problematic for the first few revisions of iOS 9, but the 6th beta of iOS 9.3 seems to have fixed most of the problems I’ve had.
  • The default “Reminders” list itself is used for everything I need to do on a particular day, but I don’t care about until that day. Recurring tasks reside here, like laundry, taking out the trash or renewing my driver’s license.

My one gripe with Reminders is a simple limitation on iOS: only manual sorting. The OS X Reminders app lets me sort easily by priority or due date, but I can only manually sort on iOS. If Apple adds a sorting feature to Reminders (like they’re doing with Notes), Reminders will finally be an app you might not scoff at.

Notes.app: for all quick note access & entry

Apple’s surprisingly pretty (to me — sorry, haters) and nimble Notes is my go-to for quick essentials: important links, high-level project plans and lists, account numbers (thanks, password lock!), stuff like that. I also use it as a less technical Drafts clone, for quick note-taking (thanks 3D Touch!) for sharing to other apps when needed. The goal here is to get to important things quickly and start writing quickly.

I’ve started to find Notes really useful for quick lists at a lower level than Reminders — for example, production & mix notes. I listen back to my demos constantly while on-the-go, and I’m constantly writing down ideas and feedback for them. I don’t want to create a single Reminders list for each song or album I’m working on — that feels too heavy — but I can create a note for the songs I’m working on, and then create a Smart Reminder about them so I don’t forget to review those notes next time I’m in the home studio.

Ulysses: for all creative / open-ended writing

Ulysses has become my ultimately creative scratchpad. Lyric ideas, blog post topics, sketches for a book I may write. The beauty of Ulysses is that it allows for endless organization, reorganization, merging, splitting and impeccable Markdown formatting of text.

In my workflow, this app (and how I use it) is especially important because it ONLY contains creative writing: blog drafts, lyrics, ideas for novel or album concepts, etc. I don’t get distracted by other life stuff when I have Ulysses open full-screen on my Mac or iPhone (like right now as I write this!), so I can actually focus on finishing that song or

Ulysses’ new iPhone app is totally invaluable, too, so I can do any of the above on the go. I didn’t at first value this since I typically need a keyboard for writing lots of text quickly — but now I can easily review my writing and rework snippets of it anywhere I like, without having to wait.

Trello: for all collaborative work

Trello is everything collaborative. Now that Trello’s iOS app is just as solid as it’s beautiful web interface (and I can jump across either via Handoff) I can easily share ideas with my collaborators or comment on theirs. I rely on this for mixing/mastering my music with my friend James, planning trips with Alicia and building apps with some of my NYC friends.

Thanks to Smart Reminders, I can also reference any board or card on a Reminders list and quickly jump back to it later. For instance, if James sends me a new mix via Trello comment, I can pull it up via push notification and then immediately tell Siri to remind me about it next time I can give it a serious listen.

Pause: for focus-switching and relaxation

Pause is one of those mindfulness apps, and I’m experimenting with it in my creative workflow. It’s allowing me to clear my head of the other life noise by just relaxing my motor functions before jumping into a recording session, new blog post or brain dump. I usually use it for a few seconds before jumping straight into a new context.


I used to think that over-organizing my life was necessary in order to achieve what I wanted to do creatively — but all I ended up with was tasks on tasks on tasks, multi-tier prioritization systems and even a literal Gantt chart at one point. All I needed was an easy way to see what was most important at any given time for a particular context, be able to act on it easily and without distraction, and discipline myself to switch contexts mindfully. This system seems to be working out well for me — let’s see how it works out over time.

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?