Migrating from Google Workspaces to Apple iCloud

July 9, 2023
remote work personal tech Google Apple iCloud

The Whole Network is Fucked Meme

It’s all just a series of tubes they said. It’s all just magic they said. The internet is filled with cave trolls asking for a toll, or a 1st born in payment in exchange for misery and torment. This wasn’t what was envisioned in the beginning of the internet, and it doesn’t have to be the future of the thing.

I’ve had a fairly complex and messy situation with how my personal online communication works. Over the decades various tools came and went, and ecosystems built and floundered. Where I’ve arrived now is the desire to still tinker as any technologist will, but to have a core series of simple tools that handle the majority of my online communications and identity, and when I want to tinker I can then create other testing environments that are more ephemeral. One challenge that really became terrible in the 2000s-2020s was the proliferation of ‘mega service’ accounts, or single identities and accounts that federated and tightly attached a number of services. In Alphabet’s case, this meant Gmail, YouTube, Google Search, Chrome, Analytics, Google Domains, and so much more. It became burdensome.

Boring is Dependable, and Dependable is Boring

This would have been a series of difficult decisions to make, but Google as a company has been losing the magic and focus that helped create its internet dominance. Apps that try to be everything for everyone are broken and uncertainty about if Google will decommission apps I depend on has led me to find a less exciting platform. I’ve taken a second look at Apple, having been an Apple user for decades as well. It’s not perfect, it still lacks features, and it’s not cheap. BUT - its user design that focuses on normal human beings who want technology augmentation within their normal lives is amazingly compelling. The tempo of releases, despite getting plenty of complaints from some, is on a human time scale. I don’t find myself wondering if one day these basic tools would be broken, or function significantly differently than they did the day before. Looking at your Zoom - nothing more heart-racing than a Zoom update right before a meeting!

I am a technologist, and I helped build this thing I bemoan. - However I think too often we do not think about the actual impact, the reason for what we are doing and why as technologists. Google’s services are often engineering-led without holding design first and foremost. Lately, engineering has succumbed to profitability and bean counting. This is the decay I have seen in so many companies when they lose their reason for existing and go zombi.

So ranting aside, I decided to move over 500GB and 20+ years of emails from Google Workspaces to iCloud. It wasn’t a fun move, but with Apple’s new support of custom domains, I was able to keep my [email protected] email I have been using for sooo long. I also moved my primary calendar to iCloud as well, since for personal use it’s more than adequate. I use Calendly for calendar management, and it supports iCloud as well, while allowing me also to query other calendars to negotiate availability with work, or other projects etc. I’ve also embraced Apple iMessage now that end-to-end encryption is supported. I still maintain a secondary secure email with prontonmail, and also Signal for more sensitive communications.

All of this works on the philosophy that if I have to sell my soul to a company to host my sensitive data, I’d like to keep the footprint as small as possible. So all of my sensitive data has left Google’s platform and now lives either in Apple, or for highly secure information offline. All of this is so notable since I started with Gmail in 2003, and now 20 years later I wave goodbye to Google for now, not sure I’ll be back.