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.