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.